Light-emitting device including fused ring compound, electronic device and electronic equipment each including light-emitting device, and fused ring compound
By introducing fused ring compound sandwich materials into the light-emitting device, the problems of insufficient color purity and driving voltage are solved, achieving more efficient energy transfer and extended service life.
Patent Information
- Application Number
- CN202511183233.4
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Priority Date
- 2024-08-23
- Filing Date
- 2025-08-22
- Publication Date
- 2026-03-03
AI Technical Summary
Existing light-emitting devices have shortcomings in terms of color purity and driving voltage, and their energy transfer efficiency needs to be improved.
Using a fused ring compound represented by Equation 1 as the interlayer material of the light-emitting device, including the emission layer, improves color purity and reduces driving voltage by improving carrier recombination and energy transfer characteristics.
The use of fused ring compounds improves the color purity and driving voltage of the light-emitting device, while also improving energy transfer efficiency and extending the device's lifespan.
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Figure CN121591764A_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority and benefit to Korean Patent Application No. 10-2024-0113739, filed on August 23, 2024, with the Korean Intellectual Property Office, the entire disclosure of which is incorporated herein by reference. Technical Field
[0003] One or more embodiments of this disclosure relate to light-emitting devices including fused-ring compounds, electronic devices and electronic equipment each including a light-emitting device, and fused-ring compounds. Background Technology
[0004] Among light-emitting devices, self-emitting devices (such as organic light-emitting devices) have superior or suitable characteristics in terms of wide viewing angle, high contrast, short response time, brightness, driving voltage, and response speed compared to other devices in the related field.
[0005] In a light-emitting device, a first electrode is arranged on a substrate, followed by a hole transport region, an emitter layer, an electron transport region, and a second electrode. Holes supplied from the first electrode move towards the emitter layer through the hole transport region, while electrons supplied from the second electrode move towards the emitter layer through the electron transport region. These charge carriers, namely holes and electrons, recombine in the emitter layer to generate excitons. Excitons can transition from an excited state and decay to the ground state, thereby generating light. Summary of the Invention
[0006] One or more aspects of embodiments of this disclosure relate to light-emitting devices including fused-ring compounds, electronic devices and electronic equipment each including a light-emitting device, and fused-ring compounds.
[0007] Other aspects will be set forth in part in the description which follows and will be apparent in part from the description, or may be learned by practice of the embodiments presented in this disclosure.
[0008] According to one or more embodiments of this disclosure, the light-emitting device includes a first electrode, a second electrode opposite to the first electrode (e.g., facing the first electrode), an interlayer between the first and second electrodes and including an emitting layer, and a fused ring compound represented by Formula 1:
[0009] Formula 1
[0010]
[0011] In Formula 1, Ar1 can be a group represented by Formula 2.
[0012] Formula 2
[0013]
[0014] Among them, in Equations 1 and 2,
[0015] CY1 to CY7 can each be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0016] W1 can be a single bond, O, S, Se, Te, or N(R). 1a ), C(R 1a (R) 1b ) or Si(R 1a (R) 1b W2 can be a single bond, O, S, Se, Te, or N (R). 2a ), C(R 2a (R) 2b ) or Si(R 2a (R) 2b W3 can be a single bond, O, S, Se, Te, or N (R). 3a ), C(R 3a (R) 3b ) or Si(R 3a (R) 3b W4 can be a single bond, O, S, Se, Te, or N (R). 4a ), C(R 4a (R) 4b ) or Si(R 4a (R) 4b ),
[0017] W5 can be a single bond, O, S, Se, Te, N(R) 5a ), C(R 5a (R) 5b ) or Si(R 5a (R) 5b ),
[0018] W6 can be a single bond, O, S, Se, Te, or N(R). 6a ), C(R 6a (R) 6b ) or Si(R 6a (R) 6b ),
[0019] a1 to a6 can each be 0 or 1 independently.
[0020] If (for example, when) a1 is 0, *-(W1) a1 -*' may not exist.
[0021] If (for example, when) a2 is 0, *-(W2) a2 -*' may not exist.
[0022] If (for example, when) a3 is 0, *-(W3) a3 -*' may not exist.
[0023] If (for example, when) a4 is 0, *-(W4) a4 -*' may not exist.
[0024] If (for example, when) a5 is 0, *-(W5) a5 -*' may not exist.
[0025] If (for example, when) a6 is 0, *-(W6) a6 -*' may not exist.
[0026] The sum of a1 to a3 can be 1 or greater.
[0027] The sum of a4 to a6 can be 1 or greater.
[0028] Y1 can be O, S, N(R8), N(Ar1), C(R8)(R9) or Si(R8)(R9).
[0029] X 11 It can be C or N, X 12 It can be C(Z) 12 ) or N, X 13 It can be C(Z) 13 ) or N, X 14 It can be C(Z) 14 ) or N, X 15 It can be C(Z) 15 ) or N, and X 16 It can be C(Z) 16 ) or N,
[0030] X 21 It can be C or N, X 22 It can be C(Z) 22 ) or N, X 23 It can be C(Z) 23 ) or N, X 24 It can be C(Z) 24 ) or N, X 25 It can be C(Z) 25 ) or N, and X 26 It can be C(Z) 26 ) or N,
[0031] X 31 To X 33 Each can be independently C or N.
[0032] X 34 It can be C(Z)34 ) or N, X 35 It can be C(Z) 35 ) or N, and X 36 It can be C(Z) 36 ) or N,
[0033] X 41 and X 42 Each can be independently C or N.
[0034] X 43 It can be C(Z) 43 ) or N, X 44 It can be C(Z) 44 ) or N, X 45 It can be C(Z) 45 ) or N, and X 46 It can be C(Z) 46 ) or N,
[0035] c1 can be an integer selected from 0 to 10.
[0036] n1 to n7 can each be an integer selected from 0 to 10 independently.
[0037] If (for example, when) n1 is 2 or greater, the number of R1s of n1 can be the same or different from each other.
[0038] If (for example, when) n² is 2 or greater, the number of R² units of n² can be the same or different from each other.
[0039] If (for example, when) n3 is 2 or greater, the number of R3s of n3 can be the same or different from each other.
[0040] If (for example, when) n4 is 2 or greater, the number of R4s of n4 can be the same or different from each other.
[0041] If (for example, when) n5 is 2 or greater, the number of R5s of n5 can be the same or different from each other.
[0042] If (for example, when) n6 is 2 or greater, the number of R6s of n6 can be the same or different from each other.
[0043] If (for example, when) n7 is 2 or greater, the number of R7s of n7 can be the same or different from each other.
[0044] Optionally, some of the n1 R1s can bond together to form a ring.
[0045] Optionally, some of the n² R² units can bond together to form a ring.
[0046] Optionally, some of the n3 R3s can bond together to form a ring.
[0047] Optionally, some of the n4 R4s can bond together to form a ring.
[0048] Optionally, some of the n5 R5s can bond together to form a ring.
[0049] Optionally, some of the n6 R6s can bond together to form a ring.
[0050] Optionally, some of the n7 R7s can bond together to form a ring.
[0051] R1 to R9, R 1a To R 6a R 1b To R 6b Z 12 To Z 16 Z 22 To Z 26 Z 34 To Z 36 and Z 43 To Z 46 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0052] R 10a Possible forms:
[0053] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, or hydrazone;
[0054] Each of the following C1-C that is not substituted or is substituted:60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof;
[0055] Each of the following C3-Cs that are not substituted or are substituted: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q)21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or
[0056] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) or -P(=O)(Q 31 (Q) 32 ),
[0057] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aryl alkyl group; or C2-C 60 Heteroaryl groups, and
[0058] In Equation 2, * represents the bonding site with the adjacent nitrogen atom.
[0059] According to one or more embodiments of this disclosure, electronic devices and electronic equipment each include a light-emitting device.
[0060] According to one or more embodiments of this disclosure, a fused ring compound represented by Formula 1 is provided. Attached Figure Description
[0061] The accompanying drawings are included to provide a further understanding of this disclosure, and are incorporated in and constitute a part of this disclosure. The drawings illustrate embodiments of the disclosure and, together with the description, serve to explain the principles of the disclosure. The above and other aspects, features, and advantages of certain embodiments of the disclosure will become more apparent from the following description taken in conjunction with the accompanying drawings, wherein:
[0062] Figure 1 This is a schematic cross-sectional view of the structure of a light-emitting device according to one or more embodiments of the present disclosure;
[0063] Figure 2 This is a schematic cross-sectional view of the structure of a light-emitting device according to one or more embodiments of the present disclosure;
[0064] Figure 3 This is a schematic cross-sectional view of the structure of a light-emitting device according to one or more embodiments of the present disclosure;
[0065] Figure 4 A schematic perspective view of an electronic device according to one or more embodiments of the present disclosure;
[0066] Figure 5 A diagram illustrating the exterior of a vehicle comprising an electronic device including a light-emitting device, according to one or more embodiments of this disclosure; and
[0067] Figures 6A to 6C Each of the following diagrams is an illustrative illustration of the interior of a vehicle according to one or more embodiments of the present disclosure. Detailed Implementation
[0068] Reference will now be made in more detail to one or more embodiments, examples of which are illustrated in the accompanying drawings, wherein throughout this disclosure, the same reference numerals refer to the same elements, and for the sake of brevity, their repeated descriptions are not provided. In this regard, the presented embodiments may take different forms and should not be construed as limited to the descriptions set forth herein. Accordingly, embodiments of this disclosure are described only by reference to the accompanying drawings to explain aspects of this disclosure. As used herein, the terms “and / or” or “or” may include any and all combinations of one or more of the associated enumerated items. Throughout this disclosure, expressions such as “at least one of…”, “one of…”, and “selected from…” modify the entire list of elements rather than individual elements of the list when preceding / following a list of elements. For example, “at least one of a, b, and c”, “selected from at least one of a, b, and c”, “selected from at least one of a to c”, etc., may indicate only a, only b, only c, both a and b (e.g., simultaneously), both a and c (e.g., simultaneously), both b and c (e.g., simultaneously), all a, b, and c, or variations thereof.
[0069] A light-emitting device according to one or more embodiments of the present disclosure may include: a first electrode; a second electrode opposite to the first electrode (e.g., facing the first electrode); an interlayer between the first electrode and the second electrode and including an emitting layer; and a fused-ring compound represented by Formula 1:
[0070] Formula 1
[0071]
[0072] In Formula 1, Ar1 can be a group represented by Formula 2.
[0073] Formula 2
[0074]
[0075] Among them, in Equations 1 and 2,
[0076] CY1 to CY7 can each be independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group,
[0077] W1 can be a single bond, O, S, Se, Te, or N(R). 1a ), C(R 1a (R) 1b ) or Si(R 1a (R) 1b W2 can be a single bond, O, S, Se, Te, or N (R). 2a ), C(R 2a (R) 2b ) or Si(R 2a (R) 2b W3 can be a single bond, O, S, Se, Te, or N (R). 3a ), C(R 3a (R) 3b ) or Si(R 3a (R) 3b W4 can be a single bond, O, S, Se, Te, or N (R). 4a ), C(R 4a (R) 4b ) or Si(R 4a (R) 4b ),
[0078] W5 can be a single bond, O, S, Se, Te, N(R) 5a ), C(R 5a (R) 5b ) or Si(R 5a (R) 5b ),
[0079] W6 can be a single bond, O, S, Se, Te, or N(R). 6a ), C(R 6a (R) 6b ) or Si(R 6a (R) 6b ),
[0080] a1 to a6 can each be 0 or 1 independently.
[0081] If (for example, when) a1 is 0, *-(W1) a1 -*' may not exist.
[0082] If (for example, when) a2 is 0, *-(W2) a2 -*' may not exist.
[0083] If (for example, when) a3 is 0, *-(W3) a3 -*' may not exist.
[0084] If (for example, when) a4 is 0, *-(W4) a4 -*' may not exist.
[0085] If (for example, when) a5 is 0, *-(W5) a5 -*' may not exist.
[0086] If (for example, when) a6 is 0, *-(W6) a6 -*' may not exist.
[0087] The sum of a1 to a3 can be 1 or greater.
[0088] The sum of a4 to a6 can be 1 or greater.
[0089] Y1 can be O, S, N(R8), N(Ar1), C(R8)(R9) or Si(R8)(R9).
[0090] X 11 It can be C or N, X 12 It can be C(Z) 12 ) or N, X 13 It can be C(Z) 13 ) or N, X 14 It can be C(Z) 14 ) or N, X 15 It can be C(Z) 15 ) or N, and X 16 It can be C(Z) 16 ) or N,
[0091] X 21 It can be C or N, X 22It can be C(Z) 22 ) or N, X 23 It can be C(Z) 23 ) or N, X 24 It can be C(Z) 24 ) or N, X 25 It can be C(Z) 25 ) or N, and X 26 It can be C(Z) 26 ) or N,
[0092] X 31 To X 33 Each can be independently C or N.
[0093] X 34 It can be C(Z) 34 ) or N, X 35 It can be C(Z) 35 ) or N, and X 36 It can be C(Z) 36 ) or N,
[0094] X 41 and X 42 Each can be independently C or N.
[0095] X 43 It can be C(Z) 43 ) or N, X 44 It can be C(Z) 44 ) or N, X 45 It can be C(Z) 45 ) or N, and X 46 It can be C(Z) 46 ) or N,
[0096] c1 can be an integer selected from 0 to 10.
[0097] n1 to n7 can each be an integer selected from 0 to 10 independently.
[0098] If (for example, when) n1 is 2 or greater, the number of R1s of n1 can be the same or different from each other.
[0099] If (for example, when) n² is 2 or greater, the number of R² units of n² can be the same or different from each other.
[0100] If (for example, when) n3 is 2 or greater, the number of R3s of n3 can be the same or different from each other.
[0101] If (for example, when) n4 is 2 or greater, the number of R4s of n4 can be the same or different from each other.
[0102] If (for example, when) n5 is 2 or greater, the number of R5s of n5 can be the same or different from each other.
[0103] If (for example, when) n6 is 2 or greater, the number of R6s of n6 can be the same or different from each other.
[0104] If (for example, when) n7 is 2 or greater, the number of R7s of n7 can be the same or different from each other.
[0105] Optionally, some of the n1 R1s can bond together to form a ring.
[0106] Optionally, some of the n² R² units can bond together to form a ring.
[0107] Optionally, some of the n3 R3s can bond together to form a ring.
[0108] Optionally, some of the n4 R4s can bond together to form a ring.
[0109] Optionally, some of the n5 R5s can bond together to form a ring.
[0110] Optionally, some of the n6 R6s can bond together to form a ring.
[0111] Optionally, some of the n7 R7s can bond together to form a ring.
[0112] R1 to R9, R 1a To R 6a R 1b To R 6b Z 12 To Z 16 Z 22 To Z 26 Z 34 To Z 36 and Z 43 To Z 46 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0113] R 10a Possible forms:
[0114] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, or hydrazone;
[0115] Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof;
[0116] Each of the following C3-Cs that are not substituted or are substituted: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or
[0117] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) or -P(=O)(Q 31 (Q) 32 ),
[0118] Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aryl alkyl group; or C2-C60 Heteroaryl groups, and
[0119] In Equation 2, * represents the bonding site with the adjacent nitrogen atom.
[0120] In one or more embodiments, the fused-ring compound represented by Formula 1 may include at least one selected from deuterium (D), -F, cyano, tert-butyl, -Si(Q1)(Q2)(Q3), pyridyl, carbazole, dibenzofuranyl, dibenzothiophenyl, biphenyl and terphenyl.
[0121] In one or more embodiments, the highest occupied molecular orbital (HOMO) energy level of the fused ring compound represented by Formula 1 may be about -5.30 eV or less or about -5.35 eV or less.
[0122] In one or more embodiments, the full width at half maximum (FWHM) of the emission spectrum of the fused ring compound represented by Formula 1 may be 10 nm or less.
[0123] In one or more embodiments, the fused-ring compound represented by Formula 1 may have an asymmetric structure.
[0124] In one or more embodiments, CY1 to CY7 may each independently be cyclopentadienyl, adamantyl, norbornel, phenyl, pentabenyl, naphthyl, azulel, indaryl, acenaphthel, finasteryl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentenyl, heptabenyl, tetraphenyl, fraxyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, indene, fluorenyl, spirodifluorenyl, benzo[a] Fluorenyl, indophenanthryl, indoanthracene, pyrroleyl, thiopheneyl, furanyl, indoleyl, benzoindoleyl, naphthoindoleyl, isoindoleyl, benzoisoindoleyl, naphthoisoindoleyl, benzothiopheneyl, benzofuranyl, carbazoleyl, dibenzothiopheneyl, dibenzothiopheneyl, dibenzofuranyl, dibenzoselenopheneyl, indocarbazoleyl, indolecarbazoleyl, benzofuranocarbazoleyl, benzothiophenecarbazoleyl, benzothiophenecarbazoleyl, benzoindoleyl Dolocarbazolyl, benzocarbazolyl, benzonaphthofuranyl, benzonaphthothiol, benzonaphthothiol, benzofuran-dibenzofuranyl, benzofuran-dibenzothiol, benzothiophene-dibenzothiol, pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl Pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinyl, cyclolinyl, phthalazinyl, naphthinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiopheneyl, or azadibenzofuranyl.
[0125] In one or more embodiments, CY1 to CY7 may each independently be phenyl, pyridyl, pentanenyl, naphthyl, azuleyl, indaryl, acenaphthel, phenanthyl, anthraceneyl, indene, fluorenyl, spirodifluorenyl, benzo[fluorenyl], indene[phenanthyl], indoleyl, benzo[indole], naphthe[indole], isoindoleyl, benzo[isoindole], naphthe[isoindole], benzo[thiophene], benzo[furanyl], carbazoleyl, di... Benzothiophenyl, dibenzothiophenyl, dibenzofuranyl, dibenzoselenophenyl, indocarbazoyl, indocarbazoyl, benzofuranocarbazoyl, benzothiophenocarbazoyl, benzothiophenocarbazoyl, benzoindocarbazoyl, benzocarbazoyl, benzonaphthiophenyl, benzonaphthiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl or benzothiophenodibenzothiophenyl.
[0126] In one or more embodiments, i) one of a1 to a3 can be 0, and the rest can each be 1, and
[0127] ii) One of a4 to a6 can be 0, and the rest can each be 1.
[0128] In one or more embodiments, the fused-ring compound represented by Formula 1 may be a compound represented by any one of Formulas 1-1 to 1-6:
[0129] Formula 1-1
[0130]
[0131] Formula 1-2
[0132]
[0133] Formula 1-3
[0134] Formula 1-4
[0135] Formula 1-5
[0136] Formula 1-6
[0137]
[0138] Among them, in equations 1-1 to 1-6,
[0139] Ar1, W1 through W6 and Y1 can each be independently identical to those described herein.
[0140] R 11 To R 14 Each can be independently identical to the description of R1 in this paper.
[0141] R 21 To R 24 Each can be independently identical to the description of R2 in this paper, and
[0142] R 31 and R 32 Each can be independently identical to the description of R3 in this paper.
[0143] R 41 To R 44 Each can be independently identical to the description of R4 in this paper.
[0144] R 51 To R 54 Each can be independently identical to the description of R5 in this paper.
[0145] R61 and R 62 Each can be independently identical to the description of R6 in this paper, and
[0146] R 71 To R 73 Each can be independently identical to the description of R7 in this document.
[0147] In one or more embodiments, a1 can be 1, a2 can be 1, a3 can be 0, a4 can be 0, a5 can be 1, and a6 can be 1.
[0148] In one or more embodiments, Ar1 may be a group represented by any one of formulas 2-1 to 2-8:
[0149] Among them, in equations 2-1 to 2-8,
[0150] Z1 to Z3, Z'1, and Z'3 can each be independently compared with Z in this paper. 12 The descriptions are the same; b1 and b2 can each be an integer selected from 0 to 5.
[0151] b3 can be an integer selected from 0 to 3, and b1' can be an integer selected from 0 to 4.
[0152] b3' can be an integer selected from 0 to 2, and
[0153] * Indicates the bonding site with an adjacent nitrogen atom.
[0154] In one or more embodiments, W1 may be N(R) 1a ),
[0155] W2 can be 0.
[0156] W5 can be O, S, Se, Te, or N(R) 5a ),and
[0157] W6 can be a single bond, O, S, or N(R) 6a ).
[0158] In one or more embodiments, Y1 may be N(Ar1).
[0159] In one or more embodiments, c1 may be 0.
[0160] In one or more embodiments, X 11 To X 16 X 21 To X 26 X 31 To X 36 and X 41 To X46 Each can be different from N.
[0161] In one or more embodiments, i) is selected from X 11 To X 16 At least one of them can be N.
[0162] ii) Selected from X 21 To X 26 At least one of them can be N, and
[0163] iii) Selected from X 31 To X 36 At least one of them can be N.
[0164] In one or more embodiments, R1 to R9 may each be independently hydrogen, deuterium, -F, cyano, unsubstituted, or modified by at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2).
[0165] In one or more embodiments, R1 to R9 can each be independently:
[0166] Hydrogen, deuterium, -F, or cyano;
[0167] Each of the following is an unsubstituted or substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, or 1,2-dimethylpropyl.
[0168] Each of the following unsubstituted or substituted fluorenyl, phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazole, azadibenzofuranyl, azadibenzothiophenyl, azacarbazole, phenoxazinyl, phenthiazinyl, or pyridoindolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, or (e.g., any suitable) combination thereof; or
[0169] -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2).
[0170] In one or more embodiments, R 1a To R 6a and R 1b To R 6b Each can be independently an unsubstituted phenyl, biphenyl, terphenyl, dibenzofuranyl, dibenzothiophenyl or carbazoleyl group, or substituted with deuterium, -F, cyano, methyl, tert-butyl, phenyl or any suitable combination thereof.
[0171] In one or more embodiments, R 1a To R 6a R 1b To R 6b R8 and R9 can be selected independently for their respective reasons.
[0172] Groups represented by any one of Formulas 3-1 to 3-13:
[0173]
[0174]
[0175] Among them, in equations 3-1 to 3-13,
[0176] T1 can be N(R'1), C(R'1)(R'2), Si(R'1)(R'2), Se, Te, O, or S.
[0177] R'1 to R'5, R'7, R”4 and R”5 can each be independently compared with R in this paper. 10a The same restrictions apply.
[0178] d3 can be an integer selected from 0 to 3.
[0179] d4 can be an integer selected from 0 to 4.
[0180] d5 can be an integer selected from 0 to 5.
[0181] d7 can be an integer selected from 0 to 7, and
[0182] * Indicates the bonding site with adjacent atoms.
[0183] In one or more embodiments, the fused-ring compound represented by Formula 1 may be any one of compound 1 to compound 80 (e.g., selected from any one of them):
[0184]
[0185]
[0186]
[0187]
[0188] Fused ring compounds may have a structure represented by Formula 1 and may include three boron-containing fused ring moieties and a substituent Ar1 bonded to the nitrogen atom constituting the fused ring. This structure can cause significant steric hindrance in the molecule, resulting in weak Dexter electron transfer properties, small Stokes shift values, and a narrow FWHM.
[0189] Accordingly, the fused-ring compound represented by Formula 1 can improve the color purity and driving voltage of the light-emitting device. Moreover, in the light-emitting device employing the fused-ring compound represented by Formula 1, energy can be easily transferred within the light-emitting device, resulting in improved lifetime characteristics.
[0190] By referring to the synthetic examples and embodiments described herein, those skilled in the art can readily or appropriately understand the method for synthesizing the fused-ring compounds represented by Formula 1.
[0191] At least one fused-ring compound represented by Formula 1 can be used in a light-emitting device (e.g., an organic light-emitting device). Therefore, one or more aspects of embodiments of this disclosure relate to a light-emitting device comprising: a first electrode; a second electrode opposite to (e.g., facing the first electrode); an interlayer between the first and second electrodes and including an emission layer; and a fused-ring compound represented by Formula 1 as described in this disclosure.
[0192] In one or more embodiments, the first electrode of the light-emitting device may be an anode.
[0193] The second electrode of the light-emitting device can be a cathode.
[0194] The interlayer may further include a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode.
[0195] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and
[0196] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
[0197] In one or more embodiments, the fused ring compound represented by Formula 1 may be included in the sandwich layer.
[0198] In one or more embodiments, the fused ring compound represented by Formula 1 may be included in the emitter layer.
[0199] In one or more embodiments, the emitter layer may include a host and a dopant, and the dopant may include a fused ring compound represented by Formula 1.
[0200] In one or more embodiments, the emitting layer may emit blue light.
[0201] In one or more embodiments, the dopant may be a phosphorescent dopant or a delayed fluorescence dopant.
[0202] In one or more embodiments, the body may include a first body containing at least one electron-donating group and a second body containing at least one electron-withdrawing group.
[0203] In one or more embodiments, the emitter layer may further include a sensitizer.
[0204] In one or more embodiments, the emission layer may include a delayed fluorescence material.
[0205] In one or more embodiments, the emitting layer may emit blue or green light.
[0206] In one or more embodiments, the emitter layer may include a first body and a second body, wherein the first body may be a hole transport compound including at least one electron-donating group, and the second body may be an electron transport compound including at least one electron-withdrawing group.
[0207] In one or more embodiments, the emitter layer may further include a third compound, and the third compound may be a metal-containing compound.
[0208] In one or more embodiments, the third compound may be used as a sensitizer (e.g., a phosphorescent sensitizer).
[0209] In one or more embodiments, the third compound may not emit light.
[0210] In one or more embodiments, the emitter layer may further include at least one of an auxiliary dopant and a sensitizer.
[0211] In one or more embodiments, the auxiliary dopant and sensitizer may each be an organometallic compound comprising Pt and a tetradentate ligand bonded to Pt, wherein the tetradentate ligand may include a carbene moiety chemically bonded to Pt. For example, the auxiliary dopant and / or sensitizer may include a third compound.
[0212] In one or more embodiments, the first and second bodies can be used as bodies for forming the excited-state complex.
[0213] As used herein, the term "electron-donating group" refers to any part that has the ability to donate electrons, for example, a C3-C group that can be rich in π electrons. 60 Cyclic groups or amine groups, but embodiments of this disclosure are not limited thereto. Electron-donating groups may refer to nitrogen-containing C1-C groups other than those lacking π electrons. 60Cyclic groups other than heterocyclic groups.
[0214] As used herein, the term "electron-withdrawing group" refers to any part that has electron-withdrawing ability, such as -F, -CFH2, -CF2H, -CF3, -CN, -NO2, and nitrogen-containing Cl-C atoms lacking π electrons. 60 Heterocyclic groups or any combination thereof. However, embodiments of this disclosure are not limited thereto.
[0215] Regarding the light emission path in the light emission device according to the embodiment, the first body and the second body can form an exciton (first process), the energy of the exciton can be transferred to a third compound (second process), and the energy can be transferred from the third compound to a fused ring compound (third process).
[0216] In one or more embodiments, the amount of the third compound may be greater than 0 parts by weight and less than 50 parts by weight, based on the total weight of 100 parts by weight of the emitter layer.
[0217] In one or more embodiments, the first body may include at least one carbazole portion, and the second body may include at least one azine portion.
[0218] In one or more embodiments, the first body may be a compound represented by formula 301-1A or formula 301-2A:
[0219] Formula 301-1A
[0220]
[0221] Formula 301-2A
[0222]
[0223] In Equations 301-1A and 301-2A,
[0224] Ring A 301 To Ring A 304 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0225] X 301 It can be O, S, N[(L 304 ) xb4 -R 304a ]、C(R 304a (R) 304b ) or Si(R 304a (R) 304b ),
[0226] X 302 Can be a single bond, O, S, N[(L 305 ) xb5 -R 305a ]、C(R 305a (R) 305b ) or Si(R 305a (R) 305b ),
[0227] X 303 Can be a single bond, O, S, N[(L 306 ) xb6 -R 306a ]、C(R 306a (R) 306b ) or Si(R 306a (R) 306b ),
[0228] xb22 and xb23 can each be an integer selected from 0 to 10 independently.
[0229] L 301 To L 307 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0230] xb1 to xb7 can each be an integer selected from 0 to 5 independently.
[0231] R 301 To R 303 R 304a To R 306a R 304b To R 306b and R 311 To R 314 Each group can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl groups, -C(Q) 301 (Q) 302 (Q) 303 ), -Si(Q 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),and
[0232] Q 301 To Q 303 Each is independently the same as described for Q1, and R 10a Same as described in this article.
[0233] In one or more embodiments, the first body may be one of compounds HTH1 to HTH56 (e.g., selected from any of them), but the embodiments of this disclosure are not limited thereto:
[0234]
[0235]
[0236]
[0237] In one or more embodiments, the second body may be a compound represented by formula 302:
[0238] Formula 302
[0239]
[0240] In Equation 302,
[0241] X 321 It can be C(R) 321 ) or N,
[0242] X 322 It can be C(R) 322 ) or N,
[0243] X323 It can be C(R) 323 ) or N,
[0244] Selected from X 321 To X 323 At least one of them can be N,
[0245] L 324 To L 326 Each can be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, *-C(Q) 321 (Q) 322 )-*'、*-Si(Q 321 (Q) 322 )-*'、*-B(Q 321 )-*' or *-N(Q 321 )-*',
[0246] n324 to n326 can each be an integer selected from 1 to 5 independently.
[0247] R 321 To R 326 Each group can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl groups, -C(Q) 323 (Q) 324 (Q) 325 ), -Si(Q 323 (Q) 324 (Q) 325 -N(Q) 323 (Q)324 -B(Q) 323 (Q) 324 -C(=O)(Q) 323 -S(=O)2(Q) 323 ) or -P(=O)(Q 323 (Q) 324 ),
[0248] Selected from Q 321 To Q 325 and R 321 To R 326 Two or more adjacent groups may optionally be bonded to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C2-C 30 Heterocyclic group,
[0249] * and *' each indicate the bonding site with the adjacent atom.
[0250] R 10a The same as described in this article, and
[0251] Q 321 To Q 325 Each is independently identical to the description for Q1.
[0252] In one or more embodiments, the second body may be one of compounds ETH1 to ETH86 (e.g., selected from any of them), but embodiments of this disclosure are not limited thereto:
[0253]
[0254]
[0255]
[0256]
[0257] In one or more embodiments, the third compound may be a compound represented by formula 401A:
[0258] Formula 401A
[0259] M 401 (L 401 ) n401 (L 402 ) n402
[0260]
[0261] Among them, in Equations 401A and 402A to 402D,
[0262] M401 can be a transition metal in the first row, the second row, or the third row of the periodic table.
[0263] L 401 It can be a ligand represented by one of formulas 402A to 402D.
[0264] L 402 It can be a monodentate, bidentate, or tripentate ligand.
[0265] n401 can be 1 or 2.
[0266] n402 can be an integer selected from 0 to 4.
[0267] A 401 To A 404 Each can be independently classified as C5-C 30 Carbocyclic or C1-C 30 Heterocyclic group,
[0268] T 401 To T 404 Each can independently be a single bond, double bond, *-O-*', *-S-*', *-C(=O)-*', *-S(=O)-*', or *-C(R)-*'. 405 (R) 406 )-*'、*-C(R 405 )=C(R 406 )-*'、*-C(R 405 )=*'、*-Si(R 405 (R) 406 )-*'、*-B(R 405 )-*'、*-N(R 405 )-*' or *-P(R 405 )-*',
[0269] k401 to k404 can each be independently 1, 2, or 3.
[0270] Y 401 To Y 404 Each can be an independent single bond (e.g., a covalent or coordinate bond), *-O-*', *-S-*', *-C(R)', etc. 407 (R) 408 )-*'、*-Si(R 407 (R) 408 )-*'、*-B(R 407 )-*'、*-N(R 407 )-*' or *-P(R407 )-*',
[0271] *1, *2, *3, and *4 each indicate M 401 The bonding sites,
[0272] R 401 To R 408 Each group can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, hydrazone, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic group, unsubstituted or with at least one R 10a Replacement C6-C 60 aryloxy, unsubstituted, or with at least one R 10a Replacement C6-C 60 Aryl thiols, unsubstituted or with at least one R 10a Replacement C7-C 60 Aryl groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2),
[0273] R 401 To R 408 They may optionally bond to each other to form unsubstituted or by at least one R 10a Replacement C5-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0274] b401 to b404 can each be an integer selected from 0 to 10 independently.
[0275] * and *' each indicate the bonding site with the adjacent atom, and
[0276] Q1 to Q3 and R10a Each is the same as described in this article.
[0277] In one or more embodiments, the compound represented by formula 401A may be a carbene complex.
[0278] As used herein, the term "carbaene complex" refers to a complex comprising a metal and a ligand bonded to the metal, wherein at least one bond between the metal and the ligand is a bond between the metal and a carbon atom of the carbaene moiety.
[0279] In one or more embodiments, the sensitizer may include a compound represented by formula 401A.
[0280] In one or more embodiments, the third compound may include at least one of compounds PD1 to PD41 (e.g., including one or any of them), but embodiments of this disclosure are not limited thereto:
[0281]
[0282]
[0283]
[0284] In one or more embodiments, R in Formula 301-1A and Formula 301-2A 301 To R 303 R 304a To R 306a R 304b To R 306b and R 311 To R 314 R in Equation 302 321 To R 326 And R in Equations 401A and 402A to 402D 401 To R 408 Each of these can be independently: hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 20 Alkyl or C1-C 20 Alkoxy;
[0285] Each of the following C1-C is replaced 20 Alkyl or C1-C 20 Alkyl groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amidine, hydrazine, hydrazone, C1-C 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, or any combination thereof;
[0286] Each of the following unsubstituted or substituted compounds: cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C) 10 Alkyl)phenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrroloyl, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazole, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, cinolinyl, carbazole, phenanthridine, acridineyl, phenanthrololyl, phenazinyl, benzimidazolyl, benzofuranyl Benzothiophene, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothiophene, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophene, azafluorenyl or azadibenzothiophene: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amido, hydrazyl, hydrazone, C1-C 20 Alkyl, C1-C 20 Alkoxy, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, biphenyl, (C1-C) 10Alkyl)phenyl, naphthyl, tetrahydronaphthyl, fluorenyl, phenanthryl, anthracene, fluoranyl, triphenylene, pyrene, 1,2-benzophenanthryl, pyrrole, thiophene, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, inzolyl, purine, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, phthalazinyl, naphthidyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, zolylinyl Carbazolyl, phenanthridinel, acridinel, phenanthrolinyl, phenazinyl, benzimidazolyl, benzofuranyl, benzothiophenel, benzoisothiazolyl, benzoxazolyl, benzoisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, thiadiazolyl, dibenzofuranyl, dibenzothiophenel, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, imidazopyrimidinyl, azacarbazolyl, azadibenzofuranyl, azadibenzothiophenel, azafluorenyl, azadibenzothiophenel, -Si(Q) 31 (Q) 32 (Q) 33 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 -P(=O)(Q) 31 (Q) 32 ) or any combination thereof; or
[0287] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1), or -P(=O)(Q1)(Q2), and
[0288] Q1 to Q3 and Q 31 To Q 33 Each is the same as described in this article.
[0289] In one or more embodiments, R in Formula 301-1A and Formula 301-2A 301 To R 303 R 304a To R 306a R 304b To R 306b and R 311 To R 314 R in Equation 302 321 To R 326 And R in Equations 401A and 402A to 402D 401 To R 408Each can be independently:
[0290] Hydrogen, deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy;
[0291] A group selected from one of Formulas 9-1 to 9-61 (e.g., any one) or a group selected from one of Formulas 10-1 to 10-348 (e.g., any one); or
[0292] -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2):
[0293]
[0294]
[0295]
[0296]
[0297]
[0298]
[0299]
[0300]
[0301]
[0302] In formulas 9-1 to 9-61 and 10-1 to 10-348, * indicates the bonding site with an adjacent atom, "Ph" represents phenyl, "D" represents deuterium, and "TMS" represents trimethylsilyl.
[0303] Q1 through Q3 are the same as those described in this paper.
[0304] In one or more embodiments, the electron transport region of the light-emitting device may include a hole-blocking layer, and the hole-blocking layer may include a phosphine oxide compound, a silicon compound, or any combination thereof. In one or more embodiments, the hole-blocking layer may directly contact the emitting layer.
[0305] In one or more embodiments, the light-emitting device may further include a capping layer disposed outside the first electrode (e.g., on the first electrode) and / or outside the second electrode (e.g., on the second electrode).
[0306] In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside the first electrode (e.g., on the first electrode) and a second capping layer located outside the second electrode (e.g., on the second electrode), and at least one of the first and second capping layers may include a fused-ring compound represented by Formula 1. Further details regarding the first and / or second capping layers can be found in the description provided herein.
[0307] In one or more embodiments, the light-emitting device may further include a first capping layer disposed outside the first electrode (e.g., on the first electrode). For example, the first capping layer may include a fused ring compound represented by Formula 1.
[0308] In one or more embodiments, the light-emitting device may further include a second capping layer disposed outside the second electrode (e.g., on the second electrode). For example, the second capping layer may include a fused-ring compound represented by Formula 1.
[0309] In one or more embodiments, the light-emitting device may further include a first capping layer disposed outside the first electrode (e.g., on the first electrode) and / or a second capping layer disposed outside the second electrode (e.g., on the second electrode). For example, at least one of the first and second capping layers may include a fused ring compound represented by Formula 1.
[0310] As used herein, the expression “(the interlayer and / or capping layer) comprises a fused-ring compound represented by Formula 1” can be understood as “(the interlayer and / or capping layer) may comprise one fused-ring compound represented by Formula 1 or two or more different kinds of fused-ring compounds each represented by Formula 1”.
[0311] In one or more embodiments, the interlayer and / or capping layer may comprise only compound 1 as a fused-ring compound. In this respect, compound 1 may be present in the emitting layer of the light-emitting device. In one or more embodiments, the interlayer may comprise both compound 1 and compound 2 as fused-ring compounds. In this respect, compound 1 and compound 2 may be present in substantially the same layer (e.g., both compound 1 and compound 2 may be present in the emitting layer simultaneously), or they may be present in different layers (e.g., compound 1 may be present in the emitting layer, and compound 2 may be present in the electron transport region).
[0312] As used herein, the term "sandwich" refers to a single layer and / or multiple layers between the first and second electrodes of a light-emitting device.
[0313] One or more aspects of embodiments of this disclosure relate to electronic devices including light-emitting devices. The electronic device may further include a thin-film transistor. For example, in one or more embodiments, the electronic device may further include a thin-film transistor comprising a source electrode and a drain electrode, wherein a first electrode of the light-emitting device is electrically connected to the source electrode or drain electrode of the thin-film transistor. In one or more embodiments, the electronic device may further include a color filter, a color conversion layer, a touchscreen layer, a polarizing layer, or any combination thereof. Further details regarding the electronic device can be found in the description provided herein.
[0314] One or more aspects of embodiments of this disclosure relate to electronic devices including light-emitting devices, and the electronic devices may be at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, indoor light, outdoor light, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, portable telephone, tablet PC, tablet computer, personal digital assistant (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, three-dimensional (3D) display, virtual reality display, augmented reality display, vehicle, video wall with multiple displays spliced together, theater screen, stadium screen, phototherapy device, and sign.
[0315] Figure 1 Description
[0316] Figure 1 This is a schematic cross-sectional view of a light-emitting device 10 according to one or more embodiments of the present disclosure. The light-emitting device 10 may include a first electrode 110, a sandwich layer 130, and a second electrode 150.
[0317] The following text will refer to Figure 1 The structure of the light-emitting device 10 according to one or more embodiments and the method of manufacturing the light-emitting device 10 are described in more detail.
[0318] First electrode 110
[0319] exist Figure 1In one or more embodiments, a substrate may be additionally provided and disposed below the first electrode 110 and / or on the second electrode 150. A glass substrate or a plastic substrate may be used as the substrate. In one or more embodiments, the substrate may be a flexible substrate and may include plastics with excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.
[0320] The first electrode 110 can be formed, for example, by depositing or sputtering a material for forming the first electrode 110 on a substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 can be a high work function material that facilitates hole injection.
[0321] The first electrode 110 may be a reflective electrode, a transmissive-reflective electrode, or a transmissive electrode. In one or more embodiments, if (for example, when) the first electrode 110 is a transmissive electrode, the material used to form the first electrode 110 may include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), or any combination thereof. In one or more embodiments, if (for example, when) the first electrode 110 is a transmissive-reflective electrode or a reflective electrode, the material used to form the first electrode 110 may include magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof.
[0322] The first electrode 110 may have a monolayer structure comprising a single layer (e.g., composed of a single layer) or a multilayer structure comprising multiple layers. In one or more embodiments, the first electrode 110 may have a three-layer structure of ITO / Ag / ITO.
[0323] mezzanine 130
[0324] The interlayer 130 may be disposed above (e.g., on) the first electrode 110. The interlayer 130 may include an emission layer.
[0325] The interlayer 130 may further include a hole transport region between the first electrode 110 and the emitter layer and an electron transport region between the emitter layer and the second electrode 150.
[0326] In one or more embodiments, in addition to one or more suitable organic materials, interlayer 130 may further include metal-containing compounds (such as organometallic compounds) and / or inorganic materials (such as quantum dots).
[0327] In one or more embodiments, the interlayer 130 may include i) two or more emitting units stacked sequentially between the first electrode 110 and the second electrode 150, and ii) a charge generation layer between adjacent emitting units in the two or more emitting units. When the interlayer 130 includes two or more emitting units and a charge generation layer as described herein, the light-emitting device 10 may be a tandem light-emitting device.
[0328] Hole transport region in interlayer 130
[0329] The hole transport region may have: i) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single material), ii) a single-layer structure comprising a single layer (e.g., composed of a single layer) of multiple materials that are different from each other (e.g., composed of multiple materials that are different from each other), or iii) a multi-layer structure comprising multiple layers of multiple materials that are different from each other.
[0330] The hole transport region may include a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof.
[0331] For example, in one or more embodiments, the hole transport region may have a multi-layer structure, including a hole injection layer / hole transport layer structure, a hole injection layer / hole transport layer / emission auxiliary layer structure, a hole injection layer / emission auxiliary layer structure, a hole transport layer / emission auxiliary layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the constituent layers in each structure are stacked sequentially from the first electrode 110 in the order described.
[0332] In one or more embodiments, the hole transport region may include a compound represented by Formula 201, a compound represented by Formula 202, or any combination thereof:
[0333] Formula 201
[0334]
[0335] Formula 202
[0336]
[0337] In Equations 201 and 202,
[0338] L 201 To L 204 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60Heterocyclic group,
[0339] L 205 It can be *-O-*', *-S-*', or *-N(Q) 201 )-*', unsubstituted or by at least one R 10a Replacement C1-C 20 Alkylene, unsubstituted, or with at least one R 10a Replacement C2-C 20 alkenyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0340] xa1 to xa4 can each be an integer selected from 0 to 5 independently.
[0341] xa5 can be an integer selected from 1 to 10.
[0342] R 201 To R 204 and Q 201 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0343] R 201 and R 202 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups (e.g., carbazole group) (e.g., see compound HT16),
[0344] R 203 and R 204 Optionally via a single bond, unsubstituted, or by at least one R 10a Substituted C1-C5 alkylene groups or unsubstituted or substituted with at least one R 10a The substituted C2-C5 alkenyl groups are linked together to form an unsubstituted or substituted compound with at least one R group. 10a Replacement C8-C 60 Polycyclic groups, and
[0345] na1 can be an integer selected from 1 to 4.
[0346] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one of the groups selected from Formula CY201 to Formula CY217:
[0347]
[0348] In formulas CY201 to CY217, R 10b and R 10c Each can be associated with R. 10a The descriptions are the same, CY ring 201 To CY 204 Each can be independently C3-C 20 Carbocyclic or C1-C 20 Heterocyclic group, and at least one hydrogen in formulas CY201 to CY217 may be unsubstituted or R-substituted. 10a replace.
[0349] In one or more embodiments, in formulas CY201 to CY217, the ring CY 201 To CY 204 Each can be independently phenyl, naphthyl, phenanthryl or anthracene.
[0350] In one or more embodiments, each of Formula 201 and Formula 202 may include at least one of the groups selected from Formula CY201 to Formula CY203.
[0351] In one or more embodiments, formula 201 may include at least one group selected from formulas CY201 to CY203 and at least one group selected from formulas CY204 to CY217.
[0352] In one or more embodiments, in formula 201, xa1 can be 1, R 201 It can be a group represented by one selected from formulas CY201 to CY203, xa2 can be 0, and R 202 It can be a group represented by one of the formulas CY204 to CY207.
[0353] In one or more embodiments, each of Formulas 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulas CY201 to CY203.
[0354] In one or more embodiments, each of Formulas 201 and 202 may not include (e.g., may exclude) any group represented by Formulas CY201 to CY203 and may include at least one of the groups selected from Formulas CY204 to CY217.
[0355] In one or more embodiments, each of Formulas 201 and 202 may not include (e.g., may exclude) any of the groups represented by Formulas CY201 to CY217.
[0356] In one or more embodiments, the hole transport region may include at least one of compounds HT1 to HT46 (e.g., including one or any of them), 4,4',4”-[tris(3-methylphenyl)phenylamino]triphenylamine (m-MTDATA), 4,4',4”-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4',4”-tris[N-(2-naphthyl)-N-phenylamino]triphenylamine (2-TNATA), N,N'-di(naphthyl-1-yl)-N,N'-diphenyl-benzidine (NPB(NPD)), β-NPB, N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-benzidine] 4,4'-diamine (TPD), spiroTPD, spiroNPB, methylated NPB, 4,4'-cyclohexylbis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-tolyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS) or any combination thereof:
[0357]
[0358]
[0359]
[0360]
[0361]
[0362] The thickness of the hole transport region can be approximately 50 angstroms. to approximately For example, about to approximately When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer can be approximately [missing information]. to approximately For example, about to approximately Furthermore, the thickness of the hole transport layer can be approximately to approximately For example, about to approximately When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within the above range, satisfactory hole transport characteristics can be obtained without significantly increasing the driving voltage.
[0363] The emission assist layer can increase luminous efficiency by compensating for the optical resonant distance according to the wavelength of the light emitted by the emission layer, and the electron blocking layer can block electron leakage from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in both the emission assist layer and the electron blocking layer.
[0364] p-dopants
[0365] In one or more embodiments, in addition to one or more of the aforementioned materials, the hole transport region may further include a charge-generating material for improving conductivity. The charge-generating material may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the hole transport region (e.g., in the form of a single layer comprising the charge-generating material, e.g., composed of the charge-generating material).
[0366] The charge-generating material can be, for example, a p-doped agent.
[0367] For example, the lowest unoccupied molecular orbital (LUMO) energy level of a p-doped agent can be less than or equal to -3.5 eV.
[0368] In one or more embodiments, the p-doper may include quinone derivatives, cyano-containing compounds, compounds comprising elements EL1 and EL2, or any combination thereof.
[0369] Non-limiting examples of quinone derivatives may include tetracyanoquinone dimethyl (TCNQ) and 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinone dimethyl (F4-TCNQ).
[0370] Non-limiting examples of cyano-containing compounds may include dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarboxynitrile (HAT-CN) and compounds represented by formula 221:
[0371]
[0372] Equation 221
[0373]
[0374] In Equation 221,
[0375] R 221 To R 223Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic groups, and
[0376] Selected from R 221 To R 223 At least one of them can be independently replaced by C3-C respectively. 60 Carbocyclic or C1-C 60 Heterocyclic groups: cyano; -F; -Cl; -Br; -I; C1-C substituted with cyano, -F, -Cl, -Br, -I or any combination thereof 20 Alkyl groups; or any combination thereof.
[0377] In a compound comprising elements EL1 and EL2, element EL1 may be a metal, a metalloid, and / or any suitable combination thereof, and element EL2 may be a nonmetal, a metalloid, and / or any suitable combination thereof.
[0378] Non-limiting examples of metals may include alkali metals (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb) and / or cesium (Cs); alkaline earth metals (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr) and / or barium (Ba); transition metals (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (… Co, rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag) and / or gold (Au); post-transition metals (e.g., zinc (Zn), indium (In) and / or tin (Sn); and / or lanthanides (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb) and / or lutetium (Lu).
[0379] Non-limiting examples of metalloids may include silicon (Si), antimony (Sb), and / or tellurium (Te).
[0380] Non-limiting examples of nonmetals may include oxygen (O) and / or halogens (e.g., F, Cl, Br and / or I, etc.).
[0381] Non-limiting examples of compounds including elements EL1 and EL2 may include metal oxides, metal halides (e.g., metal fluorides, metal chlorides, metal bromides and / or metal iodides, etc.), quasi-metal halides (e.g., quasi-metal fluorides, quasi-metal chlorides, quasi-metal bromides and / or quasi-metal iodides, etc.), metal tellurides, or any combination thereof.
[0382] Non-limiting examples of metal oxides may include tungsten oxides (e.g., WO, W2O3, WO2, WO3 and / or W2O5, etc.), vanadium oxides (e.g., VO, V2O3, VO2 and / or V2O5, etc.), molybdenum oxides (e.g., MoO, Mo2O3, MoO2, MoO3 and / or Mo2O5, etc.) and / or rhenium oxides (e.g., ReO3, etc.).
[0383] Non-limiting examples of metal halides may include alkali metal halides, alkaline earth metal halides, transition metal halides, post-transition metal halides, and / or lanthanide metal halides.
[0384] Non-limiting examples of alkali metal halides may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, and / or CsI.
[0385] Non-limiting examples of alkaline earth metal halides may include BeF2, MgF2, CaF2, SrF2, BaF2, BeCl2, MgCl2, CaCl2, SrCl2, BaCl2, BeBr2, MgBr2, CaBr2, SrBr2, BaBr2, BeI2, MgI2, CaI2, SrI2 and / or BaI2.
[0386] Non-limiting examples of transition metal halides may include titanium halides (e.g., TiF4, TiCl4, TiBr4 and / or TiI4, etc.), zirconium halides (e.g., ZrF4, ZrCl4, ZrBr4 and / or ZrI4, etc.), hafnium halides (e.g., HfF4, HfCl4, HfBr4 and / or HfI4, etc.), vanadium halides (e.g., VF3, VCl3, VBr3 and / or VI3, etc.), niobium halides (e.g., NbF3, NbCl3, NbBr3 and / or NbI3, etc.), and tantalum halides (e.g., TaF3, TaCl3, TaB, etc.). r3 and / or TaI3, etc.), chromium halides (e.g., CrF3, CrCl3, CrBr3 and / or CrI3, etc.), molybdenum halides (e.g., MoF3, MoCl3, MoBr3 and / or MoI3, etc.), tungsten halides (e.g., WF3, WCl3, WBr3 and / or WI3, etc.), manganese halides (e.g., MnF2, MnCl2, MnBr2 and / or MnI2, etc.), technetium halides (e.g., TcF2, TcCl2, TcBr2 and / or TcI2, etc.), rhenium halides (e.g., ReF2, ReCl2, ReBr2 and / or R... Iron(II) halides (e.g., FeF2, FeCl2, FeBr2 and / or FeI2), ruthenium halides (e.g., RuF2, RuCl2, RuBr2 and / or RuI2), osmium halides (e.g., OsF2, OsCl2, OsBr2 and / or OsI2), cobalt halides (e.g., CoF2, CoCl2, CoBr2 and / or CoI2), rhodium halides (e.g., RhF2, RhCl2, RhBr2 and / or RhI2), iridium halides (e.g., IrF2, IrCl2, IrBr2 and / or IrI2), and iridium halides (e.g., IrF2, IrCl2, IrBr2 and...). (e.g., NiF2, NiCl2, NiBr2 and / or NiI2), palladium halides (e.g., PdF2, PdCl2, PdBr2 and / or PdI2), platinum halides (e.g., PtF2, PtCl2, PtBr2 and / or PtI2), copper (I) halides (e.g., CuF, CuCl, CuBr and / or CuI), silver halides (e.g., AgF, AgCl, AgBr and / or AgI) and / or gold halides (e.g., AuF, AuCl, AuBr and / or AuI).
[0387] Non-limiting examples of post-transition metal halides may include zinc halides (e.g., ZnF2, ZnCl2, ZnBr2 and / or ZnI2, etc.), indium halides (e.g., InI3, etc.) and / or tin halides (e.g., SnI2, etc.).
[0388] Non-limiting examples of lanthanide metal halides may include YbF, YbF2, YbF3, SmF3, YbCl, YbCl2, YbCl3, SmCl3, YbBr, YbBr2, YbBr3, SmBr3, YbI, YbI2, YbI3, and SmI3.
[0389] Non-limiting examples of quasi-metal halides may include antimony halides (e.g., SbCl5, etc.).
[0390] Non-limiting examples of metal tellurides may include alkali metal tellurides (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te and / or Cs₂Te, etc.), alkaline earth metal tellurides (e.g., BeTe, MgTe, CaTe, SrTe and / or BaTe, etc.), transition metal tellurides (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, etc.). FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu2Te, CuTe, Ag2Te, AgTe and / or Au2Te, etc.), post-transition metal tellurides (e.g., ZnTe, etc.) and / or lanthanide metal tellurides (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe and / or LuTe, etc.).
[0391] emission layer in interlayer 130
[0392] When the light-emitting device 10 is a full-color light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer according to the sub-pixels. In one or more embodiments, the emitting layer may have a stacked structure of two or more layers selected from red, green, and blue emitting layers, wherein the two or more layers are in contact with or separated from each other to emit white light (e.g., combined white light). In one or more embodiments, the emitting layer may include two or more materials selected from red, green, and blue emitting materials, wherein the two or more materials are mixed with each other in a single layer to emit white light (e.g., combined white light).
[0393] The emitting layer may include a host and a dopant. The dopant may include phosphorescent dopant, fluorescent dopant, or any combination thereof.
[0394] Based on 100 parts by weight of the host, the amount of dopant in the emitter layer can be from about 0.01 parts by weight to about 15 parts by weight.
[0395] In one or more embodiments, the emission layer may include quantum dots.
[0396] In one or more embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may be used as a host or as a dopant in the emission layer.
[0397] The thickness of the emission layer can be approximately to approximately For example, about to approximately When the thickness of the emitting layer is within this range, excellent or suitable light-emitting characteristics can be obtained without significantly increasing the driving voltage.
[0398] main body
[0399] In one or more embodiments, the body may include a compound represented by formula 301:
[0400] Formula 301
[0401] [Ar 301 ] xb11 -[(L 301 ) xb1 -R 301 ] xb21 ,
[0402] In Equation 301,
[0403] Ar 301 and L 301 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0404] xb11 can be 1, 2, or 3.
[0405] xb1 can be an integer selected from 0 to 5.
[0406] R 301 It can be hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 Alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 301 (Q) 302 (Q) 303 -N(Q) 301 (Q) 302 -B(Q) 301 (Q) 302 -C(=O)(Q) 301 -S(=O)2(Q) 301 ) or -P(=O)(Q 301 (Q) 302 ),
[0407] xb21 can be an integer selected from 1 to 5, and
[0408] Q 301 To Q 303 Each is the same as the description for Q1.
[0409] In one or more embodiments, if (for example, when) xb11 in equation 301 is 2 or greater, then two or more Ar 301 They can be connected to each other via a single key.
[0410] In one or more embodiments, the body may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:
[0411] Formula 301-1
[0412]
[0413] Formula 301-2
[0414]
[0415] Among them, in equations 301-1 and 301-2,
[0416] Ring A 301 To Ring A 304 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0417] X 301 It can be O, S, N[(L 304) xb4 -R 304 ]、C(R 304 (R) 305 ) or Si(R 304 (R) 305 ),
[0418] xb22 and xb23 can each be 0, 1, or 2 independently.
[0419] L 301 xb1 and R 301 Each is the same as described in this article.
[0420] L 302 To L 304 Each can be independently associated with L 301 The descriptions are the same.
[0421] xb2 to xb4 can each be independently identical to the description for xb1, and
[0422] R 302 To R 305 and R 311 To R 314 Each and for R 301 The descriptions are the same.
[0423] In one or more embodiments, the body may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. In one or more embodiments, the body may include a Be complex (e.g., compound H55), a Mg complex, a Zn complex, or any combination thereof.
[0424] In one or more embodiments, the body may include: at least one of compounds H1 to H128 (e.g., including one or any of them); 9,10-bis(2-naphthyl)anthracene (ADN); 2-methyl-9,10-bis(naphthyl-2-yl)anthracene (MADN); 9,10-bis(2-naphthyl)-2-tert-butyl-anthracene (TBADN); 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP); 1,3-bis(carbazolyl-9-yl)benzene (mCP); 1,3,5-tris(carbazolyl-9-yl)benzene (TCP); or any combination thereof:
[0425]
[0426]
[0427]
[0428]
[0429]
[0430]
[0431] Phosphorescent dopants
[0432] Phosphorescent dopants may include at least one transition metal as the center metal.
[0433] Phosphorescent dopants may include monodentate ligands, dipentate ligands, tridentate ligands, tetradentate ligands, pentadentate ligands, hexadentate ligands, or any combination thereof.
[0434] Phosphorescent dopants can be electrically neutral.
[0435] In one or more embodiments, the phosphorescent dopant may comprise an organometallic compound represented by formula 401:
[0436] Formula 401
[0437] M(L 401 ) xc1 (L 402 ) xc2
[0438] Formula 402
[0439]
[0440] In Equations 401 and 402,
[0441] M can be a transition metal (e.g., Ir, Pt, Pd, Os, Ti, Au, Hf, Eu, Tb, Rh, Re, or Tm).
[0442] L 401 The ligand can be represented by Equation 402, and xc1 is 1, 2, or 3, wherein if (for example, when) xc1 is 2 or greater, two or more L 401 They can be the same or different from each other.
[0443] L 402 It can be an organic ligand, and xc2 can be 0, 1, 2, 3, or 4, wherein if (for example, when) xc2 is 2 or greater, two or more L 402 They can be the same or different from each other.
[0444] X 401 and X 402 They can be nitrogen or carbon independently.
[0445] Ring A 401 And Ring A 402 Each can be independently C3-C 60 Carbocyclic or C1-C 60Heterocyclic group,
[0446] T 401 It can be a single bond, *-O-*', *-S-*', *-C(=O)-*', *-N(Q) 411 )-*'、*-C(Q 411 (Q) 412 )-*'、*-C(Q 411 )=C(Q 412 )-*'、*-C(Q 411 )=*' or *=C(Q 411 )-*',
[0447] X 403 and X 404 Each can be an independent chemical bond (e.g., covalent or coordinate), O, S, N (Q) 413 ), B(Q) 413 ), P(Q 413 ), C(Q 413 (Q) 414 ) or Si(Q 413 (Q) 414 ),
[0448] Q 411 To Q 414 Each is the same as the description for Q1.
[0449] R 401 and R 402 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 401 (Q) 402 (Q) 403 -N(Q) 401 (Q) 402 -B(Q) 401 (Q) 402 -C(=O)(Q) 401 -S(=O)2(Q) 401 ) or -P(=O)(Q 401 (Q) 402 ),
[0450] Q 401 To Q 403 Each is the same as the description for Q1.
[0451] xc11 and xc12 can each be an integer selected from 0 to 10 independently, and
[0452] In Equation 402, * and *' each indicate the binding site with M in Equation 401.
[0453] In one or more embodiments, in formula 402, i)X 401 It can be nitrogen, and X 402 It can be carbon, or ii)X 401 and X 402 Each of them can be nitrogen.
[0454] In one or more embodiments, if (for example, when) xc1 in equation 401 is 2 or greater, then two or more L 401 The two rings A in 401 Optionally via T as a linking group 402 Connected to each other, and / or two rings A 402 Optionally via T as a linking group 403 They are interconnected (see compounds PD1 through PD4 and PD7). T 402 and T 403 Each and about T 401 The descriptions are the same.
[0455] L in Equation 401 402 It can be an organic ligand. In one or more embodiments, L 402 It may include halogens, diketone groups (e.g., acetylacetone groups), carboxylic acid groups (e.g., pyridine carboxyl groups), -C (=O), isonitrile groups, -CN groups, phosphorus-containing groups (e.g., phosphine groups and / or phosphite groups, etc.) or any combination thereof.
[0456] In one or more embodiments, the phosphorescent dopant may include, for example, at least one of compounds PD1 to PD39 (e.g., including one of them or any one selected therefrom) or any combination thereof:
[0457]
[0458]
[0459]
[0460] Fluorescent dopants
[0461] Fluorescent dopants may include amine-containing compounds, styrene-containing compounds, or any combination thereof.
[0462] For example, in one or more embodiments, the fluorescent dopant may include a compound represented by Formula 501:
[0463] Formula 501
[0464]
[0465] In Equation 501,
[0466] Ar 501 L 501 To L 503 R 501 and R 502 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0467] xd1 to xd3 can each be independently 0, 1, 2, or 3, and
[0468] xd4 can be 1, 2, 3, 4, 5 or 6.
[0469] In one or more embodiments, Ar in Formula 501 501 It can be a fused ring group in which three or more monocyclic groups are fused together (e.g., anthracene, 1,2-benzophenanthrene and / or pyrene, etc.).
[0470] In one or more embodiments, xd4 in Formula 501 may be 2.
[0471] In one or more embodiments, the fluorescent dopant may include: at least one of compounds FD1 to FD37 (e.g., including one or any of them); 4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl (DPVBi); 4,4'-bis[4-(N,N-diphenylamino)styryl]biphenyl (DPAVBi); or any combination thereof:
[0472]
[0473]
[0474]
[0475] Delayed fluorescence materials
[0476] In one or more embodiments, the emission layer may include a delayed fluorescence material.
[0477] In this paper, the delayed fluorescence material can be selected from compounds that can emit delayed fluorescence based on the delayed fluorescence emission mechanism.
[0478] Depending on the type (variety) of other materials included in the emission layer, the delayed fluorescence material included in the emission layer can act as a host or a dopant.
[0479] In one or more embodiments, the difference (e.g., the absolute value of the difference) between the triplet energy level (eV) and the singlet energy level (eV) of the delayed fluorescent material can be at least about 0 eV and no greater than about 0.5 eV. When the difference between the triplet energy level (eV) and the singlet energy level (eV) of the delayed fluorescent material satisfies the above range, the upconversion from the triplet state to the singlet state of the delayed fluorescent material can occur effectively, and therefore, the luminous efficiency of the light-emitting device 10 can be improved.
[0480] In one or more embodiments, the delayed fluorescence material may include: i) comprising at least one electron-donating group (e.g., π-electron-rich C3-C). 60 Cyclic groups, such as carbazole groups, and at least one electron-withdrawing group (e.g., sulfoxide, cyano, and / or π-electron-deficient nitrogen-containing C1-C groups). 60 Materials containing heterocyclic groups; and / or ii) C8-C cyclic groups comprising at least two cyclic groups fused together with each other while sharing boron (B). 60 Materials with polycyclic groups, for example, fused-ring compounds represented by Formula 1.
[0481] Non-limiting examples of delayed fluorescence materials may include (for example, selected from) at least one of compounds DF1 to DF14:
[0482]
[0483]
[0484] quantum dots
[0485] In one or more embodiments, the emission layer may include quantum dots.
[0486] As used herein, the term “quantum dot” refers to a crystal of a semiconductor compound and may include any material capable of emitting light at one or more appropriate emission wavelengths depending on the size of the crystal.
[0487] The diameter of the quantum dots can be, for example, in the range of about 1 nanometer (nm) to about 10 nm. In this disclosure, when the quantum dots or quantum dot particles are spherical, "diameter" indicates the particle size or average particle size, and when the particles are non-spherical, "diameter" indicates the length of the major axis or the average length of the major axis. The diameter of the particles can be measured using a scanning electron microscope or a particle size analyzer. For example, a HORIBA LA-950 laser particle size analyzer can be used as the particle size analyzer. When the particle size is measured using a particle size analyzer, the average particle size is referred to as D. 50 D 50 It refers to the average diameter of 50 vol% of particles in a particle size distribution (e.g., cumulative distribution), and refers to the value of 50% of the particle size starting from the smallest particle in a distribution curve that accumulates in the order from the smallest particle size to the largest particle size, when the total number of particles is 100%.
[0488] Quantum dots can be synthesized through wet chemical processes, metal-organic chemical vapor deposition (MOCVD), molecular beam epitaxy (MBE), or any similar process.
[0489] Wet chemistry processes involve mixing quantum dot precursor materials with an organic solvent and then growing quantum dot crystals. During quantum dot crystal growth, the organic solvent naturally acts as a dispersant coordinated on the surface of the quantum dot crystals and controls their growth. This allows the growth of quantum dot crystals to be controlled or selected using a less expensive and easier process than vapor deposition methods such as metal-organic chemical vapor deposition (MOCVD) or molecular beam epitaxy (MBE).
[0490] Quantum dots may include group II-VI semiconductor compounds, group III-V semiconductor compounds, group III-VI semiconductor compounds, group I-III-VI semiconductor compounds, group IV-VI semiconductor compounds, group IV elements or compounds and / or (e.g., any suitable) combinations thereof.
[0491] Non-limiting examples of group II-VI semiconductor compounds may include (e.g.) binary compounds such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe and / or MgS; ternary compounds such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZ nSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe and / or MgZnS; quaternary compounds such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe and / or HgZnSTe; and / or combinations thereof (e.g., any suitable combination).
[0492] Non-limiting examples of group III-V semiconductor compounds may include (e.g.,) binary compounds such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and / or InSb; ternary compounds such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and / or InPSb; quaternary compounds such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and / or InAlPSb; or any combination thereof. In one or more embodiments, the group III-V semiconductor compound may further include group II elements. Non-limiting examples of group III-V semiconductor compounds that further include group II elements may include, for example, InZnP, InGaZnP, and / or InAlZnP, etc.
[0493] Non-limiting examples of group III-VI semiconductor compounds may include (e.g.,) binary compounds such as GaS, GaSe, Ga2Se3, GaTe, InS, InSe, In2S3, In2Se3 and / or InTe; ternary compounds such as InGaS3 and / or InGaSe3; and / or combinations thereof (e.g., any suitable).
[0494] Non-limiting examples of group I-III-VI semiconductor compounds may include (for example): ternary compounds, such as AgInS, AgInS2, CuInS, CuInS2, CuGaO2, AgGaO2 and / or AgAlO2; quaternary compounds, such as AgInGaS, AgInGaS2, AgInGaSe, AgInGaSe2, CuInGaS and / or CuInGaS2; or any combination thereof.
[0495] Non-limiting examples of group IV-VI semiconductor compounds may include (e.g.,) binary compounds such as SnS, SnSe, SnTe, PbS, PbSe and / or PbTe; ternary compounds such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe and / or SnPbTe; quaternary compounds such as SnPbSSe, SnPbSeTe and / or SnPbSTe; and / or combinations thereof (e.g., any suitable combination).
[0496] Group IV elements or compounds may include: single elements, such as Si and / or Ge; binary compounds, such as SiC and / or SiGe; and / or combinations thereof (e.g., any suitable combination).
[0497] Each element included in a multi-element compound (such as binary, ternary, and quaternary compounds) may exist in the particles in a substantially uniform or non-uniform concentration.
[0498] In one or more embodiments, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or a core-shell dual structure. For example, the materials included in the core and the materials included in the shell may be different from each other.
[0499] The shell of a quantum dot can act as a protective layer to prevent chemical denaturation of the core, thus maintaining semiconductor properties, and / or as a charging layer to impart electrophoretic properties to the quantum dot. The shell can be single-layered or multi-layered. In one or more embodiments, the interface between the core and the shell can have a concentration gradient, wherein the concentration of elements present in the shell decreases towards the center of the core.
[0500] Examples of shells for quantum dots may be oxides of metals, oxides of quasi-metals, or oxides of nonmetals, semiconductor compounds, and / or combinations thereof (e.g., any suitable). Non-limiting examples of oxides of metals, oxides of quasi-metals, or oxides of nonmetals may include (e.g.) binary compounds such as SiO2, Al2O3, TiO2, ZnO, MnO, Mn2O3, Mn3O4, CuO, FeO, Fe2O3, Fe3O4, CoO, Co3O4, and / or NiO; ternary compounds such as MgAl2O4, CoFe2O4, NiFe2O4, and / or CoMn2O4; and / or combinations thereof (e.g., any suitable). Examples of semiconductor compounds are, as described herein, group II-VI semiconductor compounds; group III-V semiconductor compounds; group III-VI semiconductor compounds; group I-III-VI semiconductor compounds; group IV-VI semiconductor compounds; and / or combinations thereof (e.g., any suitable). For example, suitable semiconductor compounds as shells may include CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb and / or combinations thereof (e.g., any suitable combination).
[0501] The full width at half maximum (FWHM) of the emission spectrum of quantum dots can be about 45 nm or smaller, for example, about 40 nm or smaller, for example, about 30 nm or smaller, and within these ranges, color purity or color reproducibility can be increased. Additionally, because light emitted through quantum dots is emitted in all directions, a wider viewing angle can be improved.
[0502] In addition, quantum dots can take the form of spherical nanoparticles, cone-shaped nanoparticles, multi-armed nanoparticles, cubic nanoparticles, nanotubes, nanowires, nanofibers, or nanoplates.
[0503] Because the band gap of a quantum dot can be adjusted by controlling its size, light with one or more suitable wavelength bands can be obtained from the quantum dot emitting layer. Accordingly, by using quantum dots of different sizes, light-emitting devices that emit light with one or more suitable wavelength bands can be implemented. In one or more embodiments, the size of the quantum dot can be selected to ensure that the quantum dot emits red, green, and / or blue light. Additionally, quantum dots of suitable size can be configured to emit white light through a combination of one or more suitable colors of light.
[0504] Electron transport region in interlayer 130
[0505] The electron transport region may have: i) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single material), ii) a single-layer structure comprising a single layer (e.g., composed of a single layer) of a single material (e.g., composed of a single layer) of a single material, or iii) a multilayer structure comprising multiple layers of a multiple material.
[0506] The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0507] For example, in one or more embodiments, the electron transport region may have an electron transport layer / electron injection layer structure, a hole blocking layer / electron transport layer / electron injection layer structure, an electron control layer / electron transport layer / electron injection layer structure, or a buffer layer / electron transport layer / electron injection layer structure, wherein the constituent layers in each structure are stacked sequentially from the emission layer in the order described.
[0508] The electron transport region (e.g., a buffer layer, hole blocking layer, electron control layer, or electron transport layer in the electron transport region) may include a nitrogen-containing C1-C layer containing at least one π-deficient electron. 60 Heterocyclic group.
[0509] In one or more embodiments, the electron transport region may include a compound represented by Formula 601:
[0510] Formula 601
[0511] [Ar 601 ] xe11 -[(L 601 ) xe1 -R 601 ] xe21 ,
[0512] In Equation 601,
[0513] Ar 601 and L 601 Each can be independently unsubstituted or by at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group,
[0514] xe11 can be 1, 2, or 3.
[0515] xe1 can be 0, 1, 2, 3, 4, or 5.
[0516] R 601 It can be unsubstituted or by at least one R 10a Replacement C3-C60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -Si(Q) 601 (Q) 602 (Q) 603 -C(=O)(Q) 601 -S(=O)2(Q) 601 ) or -P(=O)(Q 601 (Q) 602 ),
[0517] Q 601 To Q 603 Each is the same as the description for Q1.
[0518] xe21 can be 1, 2, 3, 4, or 5, and
[0519] Selected from Ar 601 L 601 and R 601 At least one of them can be independently unsubstituted or by at least one R. 10a Substituted π-electron-deficient nitrogen-containing C1-C 60 Heterocyclic group.
[0520] In one or more embodiments, if (for example, when) xe11 in formula 601 is 2 or greater, two or more Ar 601 They can be connected together with a single key.
[0521] In one or more embodiments, Ar in Formula 601 601 It can be unsubstituted or by at least one R 10a Substituted anthracene group.
[0522] In one or more embodiments, the electron transport region may include a compound represented by formula 601-1:
[0523] Formula 601-1
[0524]
[0525] In Equation 601-1,
[0526] X 614 It can be N or C(R) 614 ), X 615 It can be N or C(R) 615 ), X 616 It can be N or C(R) 616 ), and selected from X 614 To X 616 At least one of them can be N,
[0527] L 611 To L 613 Each and for L 601 The descriptions are the same.
[0528] xe611 to xe613 are each the same as the description for xe1.
[0529] R 611 To R 613 Each and for R 601 The descriptions are the same, and
[0530] R 614 To R 616 Each can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 20 Alkyl, C1-C 20 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 60 Heterocyclic group.
[0531] In one or more embodiments, xe1 and xe611 to xe613 in Formula 601 and Formula 601-1 may each be 0, 1 or 2 independently.
[0532] In one or more embodiments, the electron transport region may include at least one of compounds ET1 to ET45 (e.g., including one or any of them), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxyquinoline)aluminum (Alq3), bis(2-methyl-8-hydroxyquinoline-N1,O8)-(1,1'-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), 4-(naphthyl-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), or any combination thereof:
[0533]
[0534]
[0535]
[0536] The thickness of the electron transport region can be approximately to approximately For example, about to approximately When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thickness of the buffer layer, hole blocking layer, or electron control layer can each be independently within approximately [a certain range]. to approximately (For example, about to approximately Within the range of ), and the thickness of the electron transport layer can be approximately to approximately (For example, about to approximately Within the range of the above parameters, when the thickness of the buffer layer, hole blocking layer, electronic control layer, electronic transport layer and / or electronic transport region is within the above range, satisfactory electronic transport characteristics can be obtained without significantly increasing the driving voltage.
[0537] In one or more embodiments, in addition to one or more of the materials described above, the electron transport region (e.g., the electron transport layer in the electron transport region) may further include a metallic material.
[0538] Metal-containing materials may include alkali metal complexes, alkaline earth metal complexes, or any combination thereof. The metal ion in an alkali metal complex may be Li, Na, K, Rb, or Cs ions, and the metal ion in an alkaline earth metal complex may be Be, Mg, Ca, Sr, or Ba ions. Ligands coordinated to the metal ions of the alkali metal complex or alkaline earth metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthrene, cyclopentadiene, or any combination thereof.
[0539] In one or more embodiments, the metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (Liq) or compound ET-D2:
[0540]
[0541] In one or more embodiments, the electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.
[0542] The electron injection layer may have: i) a monolayer structure comprising a single layer (e.g., composed of a single layer) comprising a single material (e.g., composed of a single material), ii) a monolayer structure comprising a single layer (e.g., composed of a single layer) comprising multiple different materials, or iii) a multilayer structure comprising multiple layers comprising multiple different materials.
[0543] The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.
[0544] The alkali metal may include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.
[0545] The alkali metal compound, the alkaline earth metal compound, and the rare earth metal compound may respectively include oxides, halides (e.g., fluorides, chlorides, bromides, and / or iodides, etc.) or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.
[0546] The alkali metal compound may include: alkali metal oxides, such as Li2O, Cs2O, and / or K2O; alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and / or KI; or any combination thereof. The alkaline earth metal compound may include alkaline earth metal oxides, such as BaO, SrO, CaO, Ba x Sr 1-x O (x is a real number satisfying 0 < x < 1) and / or Ba x Ca 1-x O (x is a real number satisfying 0 < x < 1). The rare earth metal compound may include YbF3, ScF3, Sc2O3, Y2O3, Ce2O3, GdF3, TbF3, YbI3, ScI3, TbI3, or any combination thereof. In one or more embodiments, the rare earth metal compound may include lanthanide metal tellurides. Non-limiting examples of lanthanide metal tellurides may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La2Te3, Ce2Te3, Pr2Te3, Nd2Te3, Pm2Te3, Sm2Te3, Eu2Te3, Gd2Te3, Tb2Te3, Dy2Te3, Ho2Te3, Er2Te3, Tm2Te3, Yb2Te3, and Lu2Te3.
[0547] Alkali metal complexes, alkaline earth metal complexes, and rare earth metal complexes may each include i) one of the metal ions of an alkali metal, one of the metal ions of an alkaline earth metal, and one of the metal ions of a rare earth metal, and ii) a ligand bonded to the corresponding metal ion, such as hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenidine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.
[0548] In one or more embodiments, the electron-injected layer may include (e.g., composed of): alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof as described above. In one or more embodiments, the electron-injected layer may further include organic materials (e.g., compounds represented by Formula 601).
[0549] In one or more embodiments, the electron-injected layer may include (e.g., composed of): i) an alkali metal compound (e.g., an alkali metal halide); or ii) a) an alkali metal compound (e.g., an alkali metal halide), and b) an alkali metal, alkaline earth metal, rare earth metal, or any combination thereof. In one or more embodiments, the electron-injected layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, and / or a LiF:Yb co-deposited layer, etc.
[0550] When the electron injection layer further comprises organic materials, alkali metals, alkaline earth metals, rare earth metals, alkali metal compounds, alkaline earth metal compounds, rare earth metal compounds, alkali metal complexes, alkaline earth metal complexes, rare earth metal complexes, or any combination thereof may be uniformly (e.g., substantially uniformly) or non-uniformly dispersed in the matrix comprising the organic materials.
[0551] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without significantly increasing the driving voltage.
[0552] Second electrode 150
[0553] The second electrode 150 may be disposed on the interlayer 130. The second electrode 150 may be a cathode serving as an electron injection electrode, and the material used to form the second electrode 150 may be a metal, alloy, conductive compound, or any combination thereof, each having a low work function.
[0554] The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), ytterbium (Yb), silver-ytterbium (Ag-Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmission electrode, a transmission-reflection electrode, or a reflection electrode.
[0555] The second electrode 150 may have a single-layer structure or a multi-layer structure including multiple layers.
[0556] Capping layer
[0557] In one or more embodiments, the first capping layer may be disposed outside the first electrode 110 (e.g., on the first electrode 110), and / or the second capping layer may be disposed outside the second electrode 150 (e.g., on the second electrode 150). In one or more embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are stacked sequentially in the described order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked sequentially in the described order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are stacked sequentially in the described order.
[0558] In one or more embodiments, light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can be extracted to the outside through a first electrode 110, which serves as a transmissive or reflective electrode, and a first capping layer. In one or more embodiments, light generated in the emitting layer of the interlayer 130 of the light-emitting device 10 can be extracted to the outside through a second electrode 150, which serves as a transmissive or reflective electrode, and a second capping layer.
[0559] The first and second capping layers can increase the external emission efficiency based on the principle of constructive interference. Correspondingly, the light extraction efficiency of the light-emitting device 10 increases; as a result, the luminous efficiency of the light-emitting device 10 can be increased.
[0560] Each of the first and second capping layers may include a material having a refractive index of 1.6 or greater (at 589 nm).
[0561] The first capping layer and the second capping layer can each be independently an organic capping layer including organic materials, an inorganic capping layer including inorganic materials, or an organic-inorganic composite capping layer including both organic and inorganic materials.
[0562] At least one of the first and second capping layers may (e.g., the first and second capping layers may each independently) comprise a carbocyclic compound, a heterocyclic compound, an amino-containing compound, a porphyrin derivative, a phthalocyanine derivative, a naphthyl phthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, heterocyclic compound, and amino-containing compound may each optionally be substituted with a substituent comprising O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In one or more embodiments, at least one of the first and second capping layers may (e.g., the first and second capping layers may each independently) comprise an amino-containing compound.
[0563] In one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include a compound represented by formula 201, a compound represented by formula 202, or any combination thereof.
[0564] In one or more embodiments, at least one of the first capping layer and the second capping layer may (e.g., the first capping layer and the second capping layer may each independently) include at least one of compounds HT28 to HT33 (e.g., including one or any one selected therefrom), at least one of compounds CP1 to CP6 (e.g., including one or any one selected therefrom), β-NPB, or any combination thereof:
[0565]
[0566] membrane
[0567] The fused-ring compound represented by Formula 1 may be included in one or more suitable films. Accordingly, one or more aspects of embodiments of this disclosure relate to films comprising fused-ring compounds represented by Formula 1. The film may be, for example, an optical component (or light control element) (e.g., a color filter, color conversion component, capping layer, light extraction efficiency enhancement layer, selective light absorption layer, polarizing layer and / or content dot layer, etc.), a light blocking component (e.g., a light reflecting layer and / or a light absorbing layer, etc.), and / or a protective component (e.g., an insulating layer and / or a dielectric layer, etc.).
[0568] electronic devices
[0569] The light-emitting device may be included in one or more suitable electronic devices. For example, the electronic device including the light-emitting device may be a light-emitting device and / or an authentication device, etc.
[0570] In one or more embodiments, in addition to the light-emitting device, the electronic device (e.g., the light-emitting device) may further include i) a color filter, ii) a color conversion layer, or iii) a color filter and a color conversion layer. The color filter and / or color conversion layer may be arranged in at least one direction of travel of the light emitted from the light-emitting device. For example, in one or more embodiments, the light emitted from the light-emitting device may be blue light or white light (e.g., a combination of both). A detailed description of the light-emitting device is provided above. In one or more embodiments, the color conversion layer may include quantum dots. Quantum dots may be, for example, quantum dots as described herein.
[0571] An electronic device may include a first substrate. The first substrate may include a plurality of sub-pixel regions, a color filter may include a plurality of color filter regions corresponding to the plurality of sub-pixel regions, and a color conversion layer may include a plurality of color conversion regions corresponding to the plurality of sub-pixel regions.
[0572] A pixel-defining film can be arranged between multiple sub-pixel regions to define each of the multiple sub-pixel regions.
[0573] The color filter may further include a plurality of color filter areas and a light-blocking pattern arranged between the plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and a light-blocking pattern arranged between the plurality of color conversion areas.
[0574] Multiple color filter regions (or multiple color conversion regions) may include a first region configured to emit a first color of light, a second region configured to emit a second color of light, and / or a third region configured to emit a third color of light, wherein the first color of light, the second color of light, and / or the third color of light may have different maximum emission wavelengths. In one or more embodiments, the first color of light may be red light, the second color of light may be green light, and the third color of light may be blue light. In one or more embodiments, the multiple color filter regions (or multiple color conversion regions) may include quantum dots. For example, the first region may include red quantum dots to emit red light, the second region may include green quantum dots to emit green light, and the third region may not include (e.g., may exclude) quantum dots. A detailed description of quantum dots can be found in the description provided herein. The first region, the second region, and / or the third region may each further include a scatterer.
[0575] In one or more embodiments, the light-emitting device can emit first light, a first region can absorb the first light to emit first-first-color light, a second region can absorb the first light to emit second-first-color light, and a third region can absorb the first light to emit third-first-color light. In this regard, the first-first-color light, the second-first-color light, and the third-first-color light can have different maximum emission wavelengths. For example, the first light can be blue light, the first-first-color light can be red light, the second-first-color light can be green light, and the third-first-color light can be blue light.
[0576] In one or more embodiments, in addition to the light-emitting device as described above, the electronic device may further include a thin-film transistor. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode and the drain electrode is electrically connected to a first electrode or a second electrode of the light-emitting device.
[0577] Thin-film transistors may further include gate electrodes and / or gate insulating films, etc.
[0578] The active layer may include crystalline silicon, amorphous silicon, organic semiconductors and / or oxide semiconductors, etc.
[0579] In one or more embodiments, the electronic device may further include a sealing portion for sealing the light-emitting device. The sealing portion may be disposed between the color filter and / or color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, while simultaneously (e.g., synchronously) preventing ambient air and moisture from penetrating into the light-emitting device. The sealing portion may be a sealing substrate comprising a transparent glass substrate or a plastic substrate. The sealing portion may be a thin-film encapsulation layer comprising at least one of an organic layer and an inorganic layer. When the sealing portion is a thin-film encapsulation layer, the electronic device may be flexible.
[0580] In one or more embodiments, in addition to color filters and / or color conversion layers, various functional layers may be arranged on the sealed portion, depending on the application of the electronic device. Non-limiting examples of functional layers may include a touchscreen layer and a polarizing layer. The touchscreen layer may be a pressure-sensitive touchscreen layer, a capacitive touchscreen layer, or an infrared touchscreen layer.
[0581] In addition to the light-emitting device described above, the authentication device may further include a biometric information collector. The authentication device may be, for example, a biometric authentication device that authenticates an individual using biometric information of a living person (e.g., fingertip and / or pupil, etc.).
[0582] Electronic devices may be used in displays, light sources, lighting equipment, personal computers (e.g., mobile personal computers), mobile phones, digital cameras, electronic notebooks, electronic dictionaries, video game consoles, medical tools (e.g., electronic thermometers, blood pressure monitors, blood glucose meters, pulse measuring devices, pulse wave measuring devices, electrocardiogram displays, ultrasound diagnostic devices, or endoscopic displays), fish finders, one or more suitable measuring tools, instruments (e.g., instruments for vehicles, aircraft, and ships), and / or projectors, etc.
[0583] Electronic equipment
[0584] The light-emitting device may be included in one or more suitable electronic devices.
[0585] In one or more embodiments, the electronic device including the light-emitting device may be at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, indoor light, outdoor light, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, portable telephone, tablet PC, tablet computer, personal digital assistant (PDA), wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall with multiple displays spliced together, theater screen, stadium screen, phototherapy device, and sign.
[0586] Because light-emitting devices have excellent or adequate effects in terms of luminous efficiency and long lifespan, electronic devices and electronic equipment that include light-emitting devices can have the characteristics of high brightness, high resolution and low power consumption.
[0587] Figure 2 and Figure 3 Description
[0588] Figure 2 A schematic cross-sectional view is provided to illustrate a light-emitting device according to one or more embodiments of the present disclosure.
[0589] Figure 2 The light-emitting device may include a substrate 100, a thin-film transistor (TFT), a light-emitting device, and a sealing portion 300 for sealing the light-emitting device.
[0590] The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce the penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.
[0591] The TFT may be located on the buffer layer 210. The TFT may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.
[0592] The active layer 220 may include inorganic semiconductors (such as silicon or polysilicon), organic semiconductors or oxide semiconductors, and may include source region, drain region and channel region.
[0593] A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.
[0594] The interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be disposed between the gate electrode 240 and the source electrode 260, and between the gate electrode 240 and the drain electrode 270 to insulate these electrodes from each other.
[0595] The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and drain region of the active layer 220, and the source electrode 260 and the drain electrode 270 may be arranged to contact the exposed portions of the source region and drain region of the active layer 220, respectively.
[0596] The TFT can be electrically connected to a light-emitting device to drive the light-emitting device, and can be covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. The light-emitting device may be provided on the passivation layer 280. The light-emitting device may include a first electrode 110, a sandwich layer 130, and a second electrode 150.
[0597] The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may be arranged to expose a portion of the drain electrode 270 without completely covering the drain electrode 270, and the first electrode 110 may be arranged to connect to the exposed portion of the drain electrode 270.
[0598] A pixel defining film 290, including an insulating material, may be applied to the first electrode 110. The pixel defining film 290 may expose a specific area of the first electrode 110, and an interlayer 130 may be formed within the exposed area of the first electrode 110. The pixel defining film 290 may be a polyimide-based organic film or a polyacrylic acid-based organic film. In one or more embodiments, at least some layers of the interlayer 130 may extend beyond the upper portion of the pixel defining film 290 to be arranged as a common layer.
[0599] The second electrode 150 may be on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.
[0600] The sealing portion 300 may be located on the capping layer 170. The sealing portion 300 may be disposed on the light-emitting device to protect it from moisture and / or oxygen. The sealing portion 300 may include an inorganic film, which includes silicon nitride (SiN). x ), silicon dioxide (SiO) x Indium tin oxide, indium zinc oxide, or any combination thereof; organic membranes, including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, acrylic resins (e.g., polymethyl methacrylate and / or polyacrylic acid, etc.), epoxy resins (e.g., aliphatic glycidyl ether (AGE), etc.) or any combination thereof; and / or combinations of inorganic and organic membranes (e.g., any suitable).
[0601] Figure 3 A schematic cross-sectional view illustrating a light-emitting device according to one or more embodiments of the present disclosure is shown.
[0602] Figure 3 Light-emitting devices and Figure 2 The light-emitting devices are basically the same, except that a light-shielding pattern 500 and a functional area 400 are additionally arranged on the sealed portion 300. The functional area 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of a color filter area and a color conversion area. In one or more embodiments, Figure 3 The light-emitting device included in the light-emitting device can be a series of light-emitting devices.
[0603] Figure 4 Description
[0604] Figure 4This is a schematic perspective view of an electronic device 1 including a light-emitting device according to one or more embodiments of the present disclosure. As an electronic device displaying moving or still images, the electronic device 1 may be a portable electronic device (such as a mobile phone, smartphone, tablet PC, mobile communication terminal, e-notebook computer, e-reader, portable multimedia player (PMP), navigation or ultra-mobile PC (UMPC)), and one or more suitable products (such as a television, laptop computer, monitor, billboard, or Internet of Things (IoT) device). The electronic device 1 may be such a product or a part thereof as described above. In one or more embodiments, the electronic device 1 may be a wearable device (such as a smartwatch, watch phone, glasses-type (or head-mounted display) or a part of a wearable device. However, embodiments of the present disclosure are not limited thereto. In one or more embodiments, electronic device 1 may include a vehicle's dashboard, a center information display (CID) disposed on the center console or the vehicle's dashboard, an interior rearview mirror display replacing the vehicle's side mirrors, an entertainment display for the vehicle's rear seats, a display disposed on the back of the vehicle's front seats, a head-up display (HUD) mounted on the front of the vehicle or projected onto its windshield, or a computer-generated holographic augmented reality head-up display (CGH AR HUD). For ease of explanation, Figure 4 The invention explains one or more implementations of the electronic device 1 as a smartphone.
[0605] Electronic device 1 may include a display area DA and a non-display area NDA outside the display area DA. The display device can implement an image by means of a multiple pixel array arranged in two dimensions in the display area DA.
[0606] The non-display area NDA is an area where no image is displayed and may completely surround the display area DA (e.g., around the display area DA). Drivers for providing electrical signals or power to display elements arranged in the display area DA may be arranged in the non-display area NDA. Pads for electrically connecting electronic components or printed circuit boards may be arranged in the non-display area NDA.
[0607] In electronic device 1, the length in the x-axis direction and the length (e.g., width) in the y-axis direction may be different from each other. In one or more embodiments, such as Figure 4 As shown, the length in the x-axis direction may be less than the length in the y-axis direction (e.g., width). In one or more embodiments, the length in the x-axis direction may be substantially the same as the length in the y-axis direction (e.g., width). In one or more embodiments, the length in the x-axis direction may be greater than the length in the y-axis direction (e.g., width).
[0608] Figure 5and Figures 6A to 6C Description
[0609] Figure 5 This is a schematic diagram of the exterior of a vehicle 1000, which is an electronic device including a light-emitting device, according to one or more embodiments of the present disclosure. Figures 6A to 6C Each of the above is a schematic diagram of the interior of a vehicle 1000 according to one or more embodiments.
[0610] refer to Figure 5 , Figure 6A , Figure 6B and Figure 6C Vehicle 1000 can refer to one or more suitable devices used to move an object (such as a person, object, or animal) from a point of origin to a point of destination. Vehicle 1000 can include vehicles that travel on roads or tracks, vessels that move on oceans or rivers, and / or aircraft that fly in the air using air action.
[0611] In one or more embodiments, vehicle 1000 may travel on a road or track. Vehicle 1000 may move in a particular direction depending on the rotation of at least one of its wheels. In one or more embodiments, vehicle 1000 may include a three-wheeled or four-wheeled vehicle, construction machinery, a two-wheeled vehicle, a prime mover, a bicycle, or a train traveling on a track.
[0612] Vehicle 1000 may include a body having an interior and an exterior, and a chassis, which houses mechanical equipment necessary for driving, and is otherwise separate from the body of vehicle 1000. The exterior of the vehicle 1000's body may include a front panel, hood, roof panel, rear panel, trunk, and / or pillars provided at the boundaries between doors. The chassis of vehicle 1000 may include a power generation unit, power transmission unit, drive unit, steering unit, braking unit, suspension unit, transmission unit, fuel system, front and rear wheels, and / or left and right wheels.
[0613] Vehicle 1000 may include side window glass 1100, front window glass 1200, side mirror 1300, instrument panel 1400, center console 1500, passenger seat instrument panel 1600 and display device 2.
[0614] The side window glass 1100 and the front window glass 1200 can be separated by a pillar arranged between the side window glass 1100 and the front window glass 1200.
[0615] Side window 1100 may be mounted on the side of vehicle 1000. In one or more embodiments, side window 1100 may be mounted on a door of vehicle 1000. Multiple side window 1100s may be provided and may face each other. In one or more embodiments, side window 1100 may include a first side window 1110 and a second side window 1120. In one or more embodiments, the first side window 1110 may be arranged adjacent to dashboard 1400. The second side window 1120 may be arranged adjacent to passenger seat dashboard 1600.
[0616] In one or more embodiments, the side window glass 1100 may be spaced apart and / or separated from each other in the x-axis direction or the -x-axis direction (the direction opposite to the x-axis direction). In one or more embodiments, the first side window glass 1110 and the second side window glass 1120 may be spaced apart and / or separated from each other in the x-axis direction or the -x-axis direction. For example, an imaginary straight line L connecting the side window glass 1100 may extend in the x-axis direction or the -x-axis direction. In one or more embodiments, the imaginary straight line L connecting the first side window glass 1110 and the second side window glass 1120 may extend in the x-axis direction or the -x-axis direction.
[0617] The windshield 1200 may be installed at the front of the vehicle 1000. The windshield 1200 may be arranged between the side windows 1100 that are opposite to each other (e.g., facing each other).
[0618] The side mirror 1300 provides a rear view of the vehicle 1000. The side mirror 1300 may be mounted on the exterior of the vehicle body. In one or more embodiments, a plurality of side mirrors 1300 may be provided. Any one of the plurality of side mirrors 1300 may be positioned on the outer side of the first side window 1110. Another of the plurality of side mirrors 1300 may be positioned on the outer side of the second side window 1120.
[0619] The instrument panel 1400 may be positioned in front of the steering wheel. The instrument panel 1400 may include a tachometer, speedometer, coolant temperature gauge, fuel gauge, turn signal indicator, high beam indicator, warning lights, seat belt warning lights, odometer, driving recorder, automatic transmission selection indicator, door opening warning light, oil warning light, and / or low fuel warning light.
[0620] The center console 1500 may include a control panel with multiple buttons for adjusting audio devices, air conditioning devices, and / or seat heaters. The center console 1500 may be located on one side of the instrument panel 1400.
[0621] The passenger seat instrument panel 1600 may be spaced apart from and / or separated from the instrument cluster 1400 (e.g., spaced apart or separate), and the center console 1500 may be arranged between the instrument cluster 1400 and the passenger seat instrument panel 1600. In one or more embodiments, the instrument cluster 1400 may be arranged corresponding to the driver's seat, and the passenger seat instrument panel 1600 may be arranged corresponding to the passenger seat. In one or more embodiments, the instrument cluster 1400 may be adjacent to a first side window 1110, and the passenger seat instrument panel 1600 may be adjacent to a second side window 1120.
[0622] In one or more embodiments, the display device 2 may include a display panel 3, and the display panel 3 may display images. The display device 2 may be arranged inside the vehicle 1000. In one or more embodiments, the display device 2 may be arranged between side window glass 1100s that are opposite to each other (e.g., facing each other). The display device 2 may be arranged on at least one of the instrument panel 1400, the center console 1500, and the passenger seat instrument panel 1600.
[0623] Display device 2 may include organic light-emitting display devices, inorganic electroluminescent display devices, and / or quantum dot display devices, etc. Hereinafter, as an example of display device 2 according to one or more embodiments, an organic light-emitting display device including a light-emitting device will be described; however, in embodiments, one or more suitable types (categories) of display devices as described above may be used.
[0624] refer to Figure 6A In one or more embodiments, the display device 2 may be arranged on the center console 1500. In one or more embodiments, the display device 2 may display navigation information. In one or more embodiments, the display device 2 may display information about audio settings, video settings, and / or vehicle settings.
[0625] refer to Figure 6B In one or more embodiments, the display device 2 may be arranged on the instrument panel 1400. In these embodiments, the instrument panel 1400 may display driving information, etc., via the display device 2. For example, the instrument panel 1400 may be implemented digitally. The instrument panel 1400 may digitally display vehicle information and driving information. In one or more embodiments, the tachometer pointer and gauges, as well as one or more suitable warning light icons, may be displayed via digital signals.
[0626] refer to Figure 6CIn one or more embodiments, the display device 2 may be arranged on the passenger seat instrument panel 1600. The display device 2 may be embedded in or arranged on the passenger seat instrument panel 1600. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display images related to the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500. In one or more embodiments, the display device 2 arranged on the passenger seat instrument panel 1600 may display information different from the information displayed on the instrument panel 1400 and / or the information displayed on the center console 1500.
[0627] Manufacturing method
[0628] The layers constituting the hole transport region, the emission layer, and the electron transport region can be formed in specific regions using one or more appropriate methods (such as vacuum deposition, spin coating, casting, Langmuir-Brookett (LB) deposition, inkjet printing, laser printing, and / or laser-induced thermal imaging).
[0629] When the layers constituting the hole transport region, the emitter layer, and the electron transport region are each formed by vacuum deposition, the deposition can be carried out at a deposition temperature in the range of about 100°C to about 500°C, and at a deposition temperature of about 10°C. -8 To about 10 -3 The vacuum level within the range of Tor and in approximately to approximately The deposition rate is carried out within a range that depends on the material to be included in the layer to be formed and the structure of the layer to be formed.
[0630] Terminology limitations
[0631] As used in this article, the term "C3-C" 60 "Carbocyclic group" refers to a cyclic group comprising only carbon atoms (e.g., composed of carbon atoms) and having 3 to 60 carbon atoms, and is referred to herein as "C1-C". 60 A "heterocyclic group" refers to a cyclic group having 1 to 60 carbon atoms and further including heteroatoms as cyclic atoms in addition to carbon atoms. (C3-C) 60 Carbocyclic groups and C1-C 60 The heterocyclic group can be a monocyclic group comprising one ring (e.g., consisting of one ring (exactly one ring)) or a polycyclic group in which two or more rings are fused together. In one or more embodiments, C1-C 60 The number of cyclic atoms in a heterocyclic group can range from 3 to 61.
[0632] As used herein, the term "cyclic group" may (e.g., simultaneously) include C3-C 60 Carbocyclic groups and C1-C60 Both heterocyclic groups.
[0633] As used in this article, “π-electron-rich C3-C” 60 "Cyclic group" refers to a cyclic group having 3 to 60 carbon atoms and excluding *-N=*' as a cyclic moiety, and as used herein, "a nitrogen-containing C1-C group lacking π electrons". 60 "Heterocyclic group" refers to a heterocyclic group having 1 to 60 carbon atoms and including *-N=*' as a cyclic moiety.
[0634] In one or more embodiments, C3-C 60 The carbocyclic group can be i) a T1 group or ii) a fused-ring group in which two or more T1 groups are fused together (e.g., cyclopentadienyl, adamantyl, norbornel, phenyl, pentaenyl, naphthyl, azuleyl, indaryl, acenaphthel, phenanthyl, anthraceneyl, fluoranyl, triphenylene, pyrene, 1,2-benzophenantyl, peryl, penfenyl, heptaenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubidyl, keratyl, ovoleyl, indole, fluorenyl, spirodifluorenyl, benzofluorenyl, indophenantyl, or indoanthrayl).
[0635] C1-C 60 The heterocyclic group may be i) a T2 group, ii) a fused-ring group in which two or more T2 groups are fused together, or iii) a fused-ring group in which at least one T2 group and at least one T1 group are fused together (e.g., pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzothiophene, dibenzofuranyl, indocarbazole, indolecarbazole, benzofuranyl, benzothiophenecarbazole, benzothiophenecarbazole, benzoindocarbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthothiophene, benzofuranyl, dibenzofuranyl, benzofuranyl Brønsted dibenzothiophene, benzothiophene dibenzothiophene, pyrazolyl, imidazole, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, benzimidazolyl, benzooxazolyl, benzoisooxazolyl, benzothiazolyl, benzoisothiazolyl, pyridyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzyl (e.g., benzo[i]isoquinolinyl, quinoxalinyl, benzo[i]quinoxalinyl, quinazolinyl, benzo[i]quinoxalinyl, phenanthrolinyl, cenolinyl, phthalazinyl, naphthidyl, imidazo[i]pyridinyl, imidazo[i]pyrimidinyl, imidazo[i]triazinyl, imidazo[i]pyrazinyl, imidazo[i]pyridazinyl, azacarbazoyl, azafluorenyl, azadibenzothiopheneyl, azadibenzothiopheneyl and / or azadibenzofuranyl, etc.)
[0636] C3-C rich in π electrons 60 The cyclic group may be i) a T1 group, ii) a fused ring group in which two or more T1 groups are fused together, iii) a T3 group, iv) a fused ring group in which two or more T3 groups are fused together, or v) a fused ring group in which at least one T3 group and at least one T1 group are fused together (e.g., C3-C). 60 Carbocyclic, 1H-pyrrole, thiorrole, borocyclopentadienyl, 2H-pyrrole, 3H-pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiorrole, benzothiophene, benzofuranyl, carbazole, dibenzothiorrole, dibenzothiophene, dibenzofuranyl, indole-carbazole, indole-carbazole, benzofuran-carbazole, benzothiophene-carbazole, benzothiorrole-carbazole, benzoindole-carbazole, benzocarbazole, benzonaphthofuranyl, benzonaphthophene, benzonaphthorrole, benzofuran-dibenzofuranyl, benzofuran-dibenzothiophene and / or benzothiophene-dibenzothiophene, etc.
[0637] Nitrogen-containing C1-C lacking π electrons 60 The heterocyclic group may be i) a T4 group, ii) a fused ring group in which two or more T4 groups are fused together, iii) a fused ring group in which at least one T4 group and at least one T1 group are fused together, iv) a fused ring group in which at least one T4 group and at least one T3 group are fused together, or v) a fused ring group in which at least one T4 group, at least one T1 group and at least one T3 group are fused together (e.g., pyrazolyl, imidazolyl, triazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, benzopyrazolyl, etc. Benzimidazolyl, benzoxazolyl, benzoisoxazolyl, benzothiazolyl, benzoisothiazolyl, pyridinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, benzoisoquinolinyl, quinoxalinyl, benzoquinoxalinyl, quinazolinyl, benzoquinazolinyl, phenanthrolinel, cenolinyl, phthalazinyl, naphthinyl, imidazopyridinyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, azacarbazolyl, azafluorenyl, azadibenzothiopheneyl, azadibenzothiopheneyl and / or azadibenzofuranyl, etc.
[0638] The T1 group can be cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl, cyclohexadienyl, cycloheptenyl, adamantyl, norbornyl (or bicyclo[2.2.1]heptane), norbornyl, bicyclo[1.1.1]pentane, bicyclo[2.1.1]hexane, bicyclo[2.2.2]octane, or phenyl.
[0639] The T2 group can be furanyl, thiophene, 1H-pyrrolyl, thiophene, borocyclopentadienyl, 2H-pyrrolyl, 3H-pyrrolyl, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, azathiazolyl, azaboracyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyrazinyl, triazinyl, tetraazinyl, pyrrolylalkyl, imidazolyl, dihydropyrrolyl, piperidinyl, tetrahydropyridinyl, dihydropyridinyl, hexahydropyrimidinyl, tetrahydropyrimidinyl, dihydropyrimidinyl, piperazinyl, tetrahydropyrazinyl, dihydropyrazinyl, tetrahydropyrazinyl, or dihydropyrazinyl.
[0640] The T3 group can be furanyl, thiophene, 1H-pyrrole, thiophene, or borocyclopentadienyl, and
[0641] The T4 group can be 2H-pyrrole, 3H-pyrrole, imidazolyl, pyrazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiazolyl, azirthiolyl, aziboranecyclopentadienyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, or tetraazinyl.
[0642] As used in this article, the terms "cyclic group" and "C3-C" are similar to those used in other documents. 60 "Carbocyclic group", "C1-C" 60 Heterocyclic groups, π-electron-rich C3-C 60 "Cyclic groups" or "nitrogen-containing C1-C groups lacking π electrons" 60 "Heterocyclic group" can refer to a group fused with any cyclic group, monovalent group, or polyvalent group (e.g., divalent, trivalent, and / or tetravalent groups, etc.) according to the structure of the formula using the corresponding term. In one or more embodiments, "phenyl" can be benzo[a], phenyl, and / or phenylene, etc., which can be readily understood by those skilled in the art based on the structure of a formula including "phenyl".
[0643] Unit price C3-C 60 Carbocyclic groups and monovalent C1-C 60 Non-limiting examples of heterocyclic groups may include C3-C 10 cycloalkyl, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocyclic alkenyl, C6-C 60 Aryl, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heterocyclic groups. Divalent C3-C 60 Carbocyclic groups and divalent C1-C 60 Examples of heterocyclic groups may include C3-C 10Cycloalkylene, C1-C 10 Heterocyclic alkyl, C3-C 10 Cycloalkylene, C1-C 10 Heterocyclic alkenyl, C6-C 60 aryl, C1-C 60 Hypoaryl, divalent non-aromatic fused polycyclic groups and divalent non-aromatic fused heterocyclic groups.
[0644] As used in this article, the term "C1-C" 60 "alkyl" refers to a monovalent group of a straight-chain or branched aliphatic hydrocarbon having 1 to 60 carbon atoms, and non-limiting examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodel, sec-decyl, and tert-decyl. The term "C1-C" as used herein is also relevant. 60 "alkylene" refers to C1-C 60 Alkyl groups have essentially the same structure as divalent groups.
[0645] As used in this article, the term "C2-C" 60 "Alkenyl" refers to the group formed at C2-C. 60 The alkyl group has at least one carbon-carbon double bond at its middle or end, and non-limiting examples include vinyl, propenyl, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Alkenyl" refers to C2-C 60 Alkenes are divalent groups with essentially the same structure.
[0646] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group at C2-C 60 The alkyl group has at least one monovalent hydrocarbon group with a carbon-carbon triple bond in the middle or at the end, and non-limiting examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Immyneyl" refers to C2-C 60 Alkynes are divalent groups with essentially the same structure.
[0647] As used in this article, the term "C1-C" 60 "Alkoxy" refers to the compound formed by -OA 101 (where A) 101 For C1-C 60 Alkyl groups are monovalent groups, and non-limiting examples include methoxy, ethoxy, and isopropoxy.
[0648] As used in this article, the term "C3-C" 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and non-limiting examples may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, an adamantanyl group (i.e., an adamantyl group), anorbornenyl group (i.e., an norbornyl group) (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl and / or bicyclo[2.2.2]octyl, etc. The term "C3-C" as used herein... 10 "Cycloalkylene" refers to C3-C 10 Cycloalkyl groups have divalent groups with essentially the same structure.
[0649] As used in this article, the term "C1-C" 10 "Heterocyclic alkyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms and further comprising at least one heteroatom as a cyclic atom in addition to the carbon atoms, and non-limiting examples include 1,2,3,4-oxatriazolyl, tetrahydrofuranyl, and tetrahydrothiopheneyl. The term "C1-C" as used herein is also used. 10 "Heterocyclic alkyl" refers to C1-C 10 Heterocyclic alkyl groups have divalent groups with essentially the same structure.
[0650] As used in this article, the term "C3-C" 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and being non-aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl. The term "C3-C" as used herein is also relevant. 10 "Biopylene" refers to C3-C 10 Cycloalkenyl groups are divalent groups with essentially the same structure.
[0651] As used in this article, the term "C1-C" 10 "Heterocyclic alkenyl" refers to a monovalent cyclic group having 1 to 10 carbon atoms, further comprising at least one heteroatom as a cyclic atom in addition to the carbon atoms, and having at least one double bond in its ring. C1-C 10 Non-limiting examples of heterocyclic alkenyl groups include 4,5-dihydro-1,2,3,4-oxarizolyl, 2,3-dihydrofuranyl, and 2,3-dihydrothiophenyl. As used herein, the term "C1-C..." 10 "Heterocyclic alkenyl" refers to C1-C 10 Heterocyclic alkenyl groups are divalent groups with essentially the same structure.
[0652] As used in this article, the term "C6-C" 60 "Aryl" refers to a monovalent group in a carbocyclic aromatic system having 6 to 60 carbon atoms, and as used herein in the term "C6-C". 60 "Arylene" refers to a divalent group in a carbocyclic aromatic system with 6 to 60 carbon atoms. (C6-C) 60 Non-limiting examples of aryl groups include phenyl, pentanenyl, naphthyl, azulel, indole, acenaphthel, phenanthyl, phenanthryl, anthracene, fluoranthyl, triphenylene, pyrene, 1,2-benzophenanthryl, perylene, pentanenyl, heptanenyl, tetraphenyl, framyl, hexaphenyl, pentaphenyl, rubiginyl, myristyl, and ovoleyl. When C6-C 60 Aryl and C6-C 60 When each of the aryl groups comprises two or more rings, the two or more rings can fused together.
[0653] As used in this article, the term "C1-C" 60 "Heteroaryl" refers to a monovalent group in a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. The term "C1-C" is used herein. 60 "Hypo-heteroaryl" refers to a divalent group in a heterocyclic aromatic system having 1 to 60 carbon atoms and further including at least one heteroatom as a cyclic atom in addition to carbon atoms. C1-C 60 Non-limiting examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, benzo[a]quinolinyl, isoquinolinyl, benzo[a]isoquinolinyl, quinoxalinyl, benzo[a]quinoxalinyl, quinazolinyl, benzo[a]quinazolinyl, cenolinyl, phenanthrolinel, phthalazinyl, and naphthidyl. When C1-C 60 heteroaryl and C1-C 60 When each heteroaryl group comprises two or more rings, the two or more rings can fused together.
[0654] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group having two or more rings fused together, with only carbon atoms (e.g., 8 to 60 carbon atoms) as cyclic atoms, and which, if considered as a whole, is not aromatic in its molecular structure. Non-limiting examples of monovalent nonaromatic fused polycyclic groups include indenyl, fluorenyl, spirodifluorenyl, benzo[a]fluorenyl, indeno[a]phenanthryl, and indeno[a]anthrayl. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused polycyclic group.
[0655] As used herein, the term “monovalent nonaromatic fused heterocyclic group” refers to a monovalent group having two or more rings fused together, further comprising at least one heteroatom as a cyclic atom in addition to carbon atoms (e.g., 1 to 60 carbon atoms), and having no aromaticity in its molecular structure if (e.g., when) considered as a whole. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include pyrrole, thiophene, furanyl, indole, benzoindole, naphthoindole, isoindole, benzoisoindole, naphthoisoindole, benzothiophene, benzofuranyl, carbazole, dibenzothiophene, dibenzothiophene, dibenzofuranyl, azacarbazole, azafluorenyl, azadibenzothiophene, azadibenzothiophene, azadibenzofuranyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, isothiazolyl, oxadiazolyl, thiazolyl, thiazolyl Azolyl, benzopyrazolyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzooxadiazolyl, benzothiadiazolyl, imidazopyridyl, imidazopyrimidinyl, imidazotriazinyl, imidazopyrazinyl, imidazopyridazinyl, indolecarbazolyl, indolocarbazolyl, benzofuranocarbazolyl, benzothiophenocarbazolyl, benzothiophenocarbazolyl, benzoindolocarbazolyl, benzocarbazolyl, benzonaphthiophenyl, benzonaphthiophenyl, benzofuranodibenzofuranyl, benzofuranodibenzothiophenyl, and benzothiophenodibenzothiophenyl. As used herein, the term "divalent nonaromatic fused heteropolycyclic group" refers to a divalent group having substantially the same structure as a monovalent nonaromatic fused heteropolycyclic group.
[0656] As used in this article, the term "C6-C" 60 "Aryloxy group" refers to -OA 102 (where A) 102 For C6-C 60 Aryl), and as used herein by the term "C6-C" 60 "Arylthio" refers to -SA 103 (where A) 103 For C6-C 60 Aryl).
[0657] As used in this article, the term "C7-C" 60 "Aryl group" refers to -A 104 A 105 (where A) 104 For C1-C 54 Alkylene, and A 105 For C6-C 59 Aryl), and as used herein by the term "C2-C 60 "Heteroarylene" refers to -A 106 A 107 (where A) 106For C1-C 59 Alkylene, and A 107 For C1-C 59 (Miscellaneous aromatic compounds).
[0658] As used in this article, the term "C3-C" 60 "Carbocyclic group" includes C3-C 50 carbonyl group, C3-C 40 carbonyl group, C3-C 30 carbonyl group, C3-C 20 carbonyl group or C3-C 10 carbon cyclo group;
[0659] The term "C1-C" 60 "Heterocyclic groups" include C1-C 50 Heterocyclic groups, C1-C 40 Heterocyclic groups, C1-C 30 Heterocyclic groups, C1-C 20 Heterocyclic groups or C1-C 10 Heterocyclic groups;
[0660] The term "C1-C" 60 "alkyl" includes C1-C 50 Alkyl, C1-C 30 Alkyl, C1-C 20 Alkyl or C1-C 10 alkyl;
[0661] The term "C2-C" 60 "Alkenyl" includes C2-C 30 alkenyl, C2-C 20 alkenyl or C2-C 10 alkenyl;
[0662] The term "C2-C" 60 "Alkyne group" includes C2-C 30 alkynyl group, C2-C 20 alkynyl or C2-C 10 alkynyl group;
[0663] The term "C1-C" 60 "Alkoxy" includes C1-C 30 Alkoxy, C1-C 20 Alkoxy or C1-C 10 Alkoxy;
[0664] The term "C6-C" 60 "Aryl" includes C6-C 50 Aryl, C6-C 40 Aryl, C6-C 30 Aryl, C6-C 20 Aryl or C6-C 15Aryl;
[0665] The term "C1-C" 60 "Heteroary aryl" includes C1-C 50 heteroaryl, C1-C 40 heteroaryl, C1-C 30 heteroaryl, C1-C 20 heteroaryl or C1-C 10 Mixed aromatics;
[0666] "Monovalent non-aromatic fused polycyclic groups" include C8-C 60 Monovalent non-aromatic fused polycyclic groups, C8-C 50 Monovalent non-aromatic fused polycyclic groups, C8-C 40 Monovalent non-aromatic fused polycyclic groups, C8-C 30 Monovalent non-aromatic fused polycyclic groups or C8-C 20 Monovalent non-aromatic fused polycyclic groups;
[0667] The term "monovalent non-aromatic fused heterocyclic group" includes C1-C 60 Monovalent non-aromatic fused heterocyclic groups, C1-C 50 Monovalent non-aromatic fused heterocyclic groups, C1-C 40 Monovalent non-aromatic fused heterocyclic groups, C1-C 30 Monovalent non-aromatic fused heterocyclic groups or C1-C 20 Monovalent non-aromatic fused heterocyclic groups;
[0668] The term "C6-C" 60 "Aryloxy groups" include C6-C 50 Aryloxy group, C6-C 40 Aryloxy group, C6-C 30 Aryloxy group, C6-C 20 aryloxy or C6-C 15 aryloxy;
[0669] The term "C6-C" 60 "Arylthio" includes C6-C 50 Arylthio, C6-C 40 Arylthio, C6-C 30 Arylthio, C6-C 20 Aryl thiols or C6-C 15 Arylthio;
[0670] The term "C7-C" 60 "Aryl" includes C7-C 50 Aryl group, C7-C 40 Aryl group, C7-C 30 Aryl group, C7-C 20 Aryl or C7-C15 Aryl alkyl groups; and
[0671] The term "C2-C" 60 "Heteroarylene" includes C2-C 50 Heteroaryl, C2-C 40 Heteroaryl, C2-C 30 Heteroaryl, C2-C 20 Heteroaryl or C2-C 15 Heteroalkyl groups.
[0672] As used in this article, the term "R" 10a "refer to:
[0673] Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, or hydrazone;
[0674] Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 alkynyl or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof;
[0675] Each of the following C3-Cs that are not substituted or are substituted: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 Heteroaryl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or
[0676] -Si(Q 31 (Q) 32 (Q) 33 -N(Q) 31 (Q) 32 -B(Q) 31 (Q) 32 -P(Q) 31 (Q) 32 -C(=O)(Q) 31 -S(=O)2(Q) 31 ) or -P(=O)(Q 31 (Q) 32 ).
[0677] As used in this article, Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each can be independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aryl alkyl group; or C2-C 60 Heteroalkyl groups.
[0678] As used herein, the term "heteroatom" refers to any atom other than carbon and hydrogen. Non-limiting examples of heteroatoms include O, S, N, P, Si, B, Ge, Se, or any combination thereof.
[0679] As used herein, the term "first row transition metals" may include scandium (Sc), titanium (Ti), vanadium (V), chromium (Cr), manganese (Mn), iron (Fe), cobalt (Co), nickel (Ni), copper (Cu), and / or zinc (Zn), etc. The term "second row transition metals" as used herein may include yttrium (Y), zirconium (Zr), niobium (Nb), molybdenum (Mo), technetium (Tc), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), and / or cadmium (Cd), etc. The term "third row transition metals" as used herein may include hafnium (Hf), tantalum (Ta), tungsten (W), rhenium (Re), osmium (Os), iridium (Ir), platinum (Pt), and / or gold (Au), etc.
[0680] As used herein, the term "Ph" refers to phenyl, "Me" refers to methyl, "Et" refers to ethyl, and "tert-Bu" or "Bu" refers to ethyl. t "Refers to tert-butyl, and as used herein, the term "OMe" refers to methyl methacrylate (MMA).
[0681] As used herein, the term "biphenyl" refers to a phenyl group that has been substituted with a phenyl group. For example, "biphenyl" is a phenyl group having a C6-C2 configuration. 60 Aryl groups are substituted phenyl groups.
[0682] As used herein, the term "terphenyl" refers to a phenyl group substituted with a biphenyl group. For example, "terphenyl" is a phenyl group having a C6-C substituted biphenyl group. 60 Aryl-substituted C6-C 60 Aryl groups are substituted phenyl groups.
[0683] Unless otherwise specified, as used herein, * and *' each refer to the bonding site with an adjacent atom in the corresponding formula or part.
[0684] As used herein, the terms “x-axis,” “y-axis,” and “z-axis” are not limited to the three axes in an orthogonal coordinate system and can be interpreted in a broader sense than the three axes in an orthogonal coordinate system described above. For example, the x-axis, y-axis, and z-axis can describe axes that are orthogonal to each other, or they can describe axes in different directions that are not orthogonal to each other.
[0685] In this specification, "integers selected from 0 to 10" refers to integers selected from 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. The above description of numerical ranges also applies to any other numerical ranges appearing in this specification, such as integers selected from 0 and 1, integers selected from 0 to 2, integers selected from 0 to 3, integers selected from 0 to 4, integers selected from 0 to 5, integers selected from 0 to 6, integers selected from 0 to 7, integers selected from 0 to 8, integers selected from 0 to 9, and integers selected from 0 to 10, etc.
[0686] The fused-ring compounds according to one or more embodiments and the light-emitting devices according to one or more embodiments will be described in more detail below with reference to the following synthetic examples and embodiments. The phrase "using B instead of A" used in describing the synthetic examples means using substantially the same molar equivalent of B instead of A.
[0687] Example
[0688] Synthesis Example 1 (Compound 2)
[0689]
[0690] Synthesis of intermediate compound 2-a
[0691] Under an argon atmosphere, N1,N3-bis([1,1':3',1”-terphenyl]-2'-yl)-5-(tert-butyl)phenyl-1,3-diamine (10 g, 16 mmol), 1-(3-(tert-butyl)-5-(3-iodophenoxy-2,4,5-d3)phenoxy-2,4,6-d3)benzene-2,3,4,5,6-d5 (7.3 g, 16 mmol), tris(dibenzylideneacetone)dipalladium(0)(Pd2dba3) (1.6 g, 1.9 mmol), tritert-butylphosphine (P(t-Bu)3) (1.6 mL, 3.8 mmol) and sodium tert-butoxide (Na) were added. tBuO (5.8 g, 60 mmol) was added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 2-a (white solid, 11 g, yield: 73%).
[0692] Electrospray ionization liquid chromatography-mass spectrometry (ESI-LCMS): [M] + :C 68 H 49 D 11N2O2, 947.5338.
[0693] Synthesis of intermediate compound 2-b
[0694] Under an argon atmosphere, intermediate compound 2-a (11 g, 11.6 mmol), N-(3-iodo-5-(phenoxy-d5)phenyl-2,4-d2)-N-(phenyl-d5)-[1,1':3',1”-terphenyl]-2'-amine (7.3 g, 8.8 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to a 2 L flask and... It was dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 2-b (white solid, 11.4 g, yield: 68%).
[0695] ESI-LCMS: [M] + :C 104 H 62 D 23 N3O3, 1446.8084.
[0696] Synthesis of Compound 2
[0697] Under an argon atmosphere, intermediate compound 2-b (11 g, 7.6 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 hours. After cooling, triethylamine was added to terminate the reaction. The solvent was removed under reduced pressure, and the resulting solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to yield compound 2 (yellow solid, 2.8 g, yield: 25%).
[0698] ESI-LCMS: [M] + :C 104 H 59 D 17 B3N3O3, 1464.7259.
[0699] Proton nuclear magnetic resonance spectroscopy ( 1H-NMR) (CDCl3): d=8.20(m,4H),7.44(m,18H),7.32(t,3H),7.08(m,12H),7.00(s,2H),1.40(s,9H),1.26(s,9H).
[0700] Synthesis Example 2 (Compound 12)
[0701]
[0702] Synthesis of intermediate compound 12-a
[0703] Under an argon atmosphere, intermediate compound 2-a (10 g, 10.5 mmol), N-([1,1'-biphenyl]-4-yl-d9)-N-(3-(([1,1'-biphenyl]-4-yl-d9)oxy)-5-iodophenyl-4,6-d2)-[1,1':3',1”-tert-phenyl]-2'-amine (8.3 g, 10.5 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mL) were prepared. The solution was added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 12-a (white solid, 10.8 g, yield: 71%).
[0704] ESI-LCMS: [M] + :C 116 H 62 D 31 N3O3, 1606.9283.
[0705] Synthesis of Compound 12
[0706] Under an argon atmosphere, intermediate compound 12-a (10 g, 6.2 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 hours. After cooling, triethylamine was added to terminate the reaction. The solvent was removed under reduced pressure, and the resulting solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to yield compound 12 (yellow solid, 3.1 g, yield: 31%).
[0707] ESI-LCMS: [M]+ :C 116 H 59 D 25 B3N3O3, 1624.8413.
[0708] 1 H-NMR (CDCl3): d=8.17(m,4H),7.45(m,18H),7.39(m,3H),7.11(m,12H),7.00(s,2H),1.35(s,9H),1.28(s,9H).
[0709] Synthesis Example 3 (Compound 17)
[0710]
[0711] Synthesis of intermediate compound 17-a
[0712] Under an argon atmosphere, intermediate compound 2-a (10 g, 10.5 mmol), N-(3-chlorophenyl-2,4,5,6-d4)-N-(3-iodo-5-(phenoxy-d5)phenyl-2,4-d2)-[1,1':3',1”-terphenyl]-2'-amine (6.9 g, 10.5 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to 2... The solution was placed in a L-shaped flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 17-a (white solid, 10.8 g, yield: 70%).
[0713] ESI-LCMS: [M] + :C 104 H 62 D 22 ClN3O3, 1479.7602.
[0714] Synthesis of intermediate compound 17-b
[0715] Under an argon atmosphere, intermediate compound 17-a (10 g, 6.7 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 hours. After cooling, triethylamine was added to terminate the reaction. The solvent was removed under reduced pressure, and the resulting solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvents to yield intermediate compound 17-b (yellow solid, 2.4 g, yield: 24%).
[0716] ESI-LCMS: [M] + :C 104 H 59 D 16 B3ClN3O3, 1497.6876.
[0717] Synthesis of Compound 17
[0718] Under an argon atmosphere, intermediate compound 17-b (2.4 g, 1.6 mmol), 9H-carbazole-1,2,3,4,5,6,7,8-d8 (0.3 g, 1.6 mmol), Pd2dba3 (0.15 g, 0.16 mmol), tri-tert-butylphosphine (0.15 mL, 0.32 mmol), and sodium tert-butoxide (0.35 g, 4 mmol) were added to a 2 L flask and then dissolved in 20 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain compound 17 (yellow solid, 1.9 g, yield: 74%).
[0719] ESI-LCMS: [M] + :C 116 H 59 D 24 B3N4O3, 1636.8325.
[0720] 1 H-NMR (CDCl3): d=8.19(m,4H),7.43(m,18H),7.38(m,3H),7.10(m,12H),7.03(s,2H),1.41(s,9H),1.32(s,9H).
[0721] Synthesis Example 4 (Compound 28)
[0722]
[0723] Synthesis of intermediate compound 28-a
[0724] Under an argon atmosphere, N1,N3-bis([1,1':3',1”-terphenyl]-2'-yl)phenyl-4,5,6-d3-1,3-diamine (10 g, 17.6 mmol), 1-(3-(3-iodophenoxy-2,4,5-d3)phenoxy-2,4,5,6-d4)phenyl-2,3,4,5,6-d5 (7 g, 17.6 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mL) were added. (mmol) was added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 28-a (white solid, 11 g, yield: 75%).
[0725] ESI-LCMS: [M] + :C 60 H 29 D 15 N2O2, 840.1228.
[0726] Synthesis of intermediate compound 28-b
[0727] Under an argon atmosphere, intermediate compound 28-a (11 g, 13 mmol), N-(3-iodo-5-(phenoxy-d5)phenyl-2,4-d2)-N-(phenyl-d5)-[1,1':3',1”-terphenyl]-2'-amine (4.3 g, 13 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to a 2 L flask and... Dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 28-b (white solid, 12 g, yield: 69%).
[0728] ESI-LCMS: [M]+ :C 96 H 42 D 27 N3O3, 1338.7059.
[0729] Synthesis of Compound 28
[0730] Under an argon atmosphere, intermediate compound 28-b (12 g, 9 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 h. After cooling, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to yield compound 28 (yellow solid, 2.7 g, yield: 22%).
[0731] ESI-LCMS: [M] + :C 96 H 39 D 21 B3N3O3. 1356.6259.
[0732] 1 H-NMR (CDCl3): d=8.23(m,4H),7.41(m,18H),7.39(m,3H),7.08(m,12H).
[0733] Synthesis Example 5 (Compound 35)
[0734]
[0735] Synthesis of intermediate compound 35-a
[0736] Under an argon atmosphere, N3,N5-bis([1,1':3',1”-terphenyl]-2'-yl)-[1,1'-biphenyl]-2',3',4',5',6'-d5-3,5-diamine (10 g, 15.4 mmol), 3-(3-iodophenoxy-2,4,5-d3)-5-(phenoxy-d5)-1,1'-biphenyl-2,2',3',4,4',5',6,6'-d8 (7.4 g, 15.4 mmol), Pd2dba3 (1.6 g, 1.9 mmol), and tri-tert-butylphosphine (1.6 mL, 3.8 mmol) were added. Sodium tert-butoxide (5.8 g, 60 mmol) was added to a 2 L flask and then dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 35-a (white solid, 11.8 g, yield: 77%).
[0737] ESI-LCMS: [M] + :C 72 H 31 D 21 N2O2, 997.5340.
[0738] Synthesis of intermediate compound 35-b
[0739] Under an argon atmosphere, intermediate compound 35-a (11 g, 11 mmol), N-(3-iodo-5-(phenoxy-d5)phenyl-2,4-d2)-N-(phenyl-d5)-[1,1':3',1”-terphenyl]-2'-amine (6.9 g, 11 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to a 2 L flask and... Dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 35-b (white solid, 9.7 g, yield: 59%).
[0740] ESI-LCMS: [M] + :C 108 H44 D 33 N3O3, 1496.8035.
[0741] Synthesis of Compound 35
[0742] Under an argon atmosphere, intermediate compound 35-b (9 g, 6 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 hours. After cooling, triethylamine was added to terminate the reaction. The solvent was removed under reduced pressure, and the resulting solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to yield compound 35 (yellow solid, 2.3 g, yield: 26%).
[0743] ESI-LCMS: [M] + :C 108 H 41 D 27 B3N3O3, 1514.7208.
[0744] 1 H-NMR (CDCl3): d=8.11 (m, 4H), 7.39 (m, 3H), 7.35 (m, 18H), 7.08 (m, 12H), 6.99 (s, 2H).
[0745] Synthesis Example 6 (Compound 62)
[0746]
[0747] Synthesis of intermediate compound 62-a
[0748] Under an argon atmosphere, N1,N3-bis([1,1':3',1”-terphenyl]-2'-yl)-5-(tert-butyl)phenyl-1,3-diamine (10 g, 16 mmol), N-(3-(tert-butyl)-5-(3-iodophenoxy-2,4,5-d3)phenyl-2,4,6-d3)-N-(phenyl-d5)-[1,1':3',1”-terphenyl]-2'-amine (10.9 g, 16 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 62-a (white solid, 12 g, yield: 62%).
[0749] ESI-LCMS: [M] + :C 86 H 62 D 11 N3O, 1174.6484.
[0750] Synthesis of intermediate compound 62-b
[0751] Under an argon atmosphere, intermediate compound 62-a (12 g, 10 mmol), N-([1,1'-biphenyl]-3-yl-d9)-N-(3-(([1,1'-biphenyl]-4-yl-d9)oxy)-5-iodophenyl-4,6-d2)-[1,1':3',1”-tert-phenyl]-2'-amine (8 g, 10 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were prepared. The solution was added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 62-b (white solid, 12.8 g, yield: 70%).
[0752] ESI-LCMS: [M] + :C134 H 75 D 31 N4O2, 1834.0383.
[0753] Synthesis of Compound 62
[0754] Under an argon atmosphere, intermediate compound 62-b (12 g, 6.5 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 h. After cooling, triethylamine was added to terminate the reaction, and the solvent was removed under reduced pressure. The obtained solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to yield compound 62 (yellow solid, 2.6 g, yield: 21%).
[0755] ESI-LCMS: [M] + :C 134 H 72 D 25 B3N4O2, 1851.8501.
[0756] 1 H-NMR (CDCl3): d=8.21(m,8H),7.45(m,24H),7.40(t,4H),7.11(m,16H),6.88(s,2H),1.36(s,9H),1.29(s,9H).
[0757] Synthesis Example 7 (Compound 64)
[0758]
[0759] Synthesis of intermediate compound 64-a
[0760] Under an argon atmosphere, N1,N3-bis([1,1':3',1”-tert-phenyl]-2'-yl)-5-(tert-butyl)phenyl-1,3-diamine (10 g, 16 mmol), (3-(tert-butyl)-5-((3-iodophenyl-2,4,5-d3)thio)phenyl-2,4,6-d3)(phenyl-d5)thione (7.8 g, 16 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tritert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mL) were added. The solution was added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 64-a (white solid, 9.2 g, yield: 59%).
[0761] ESI-LCMS: [M] + :C 68 H 49 D 11 N2S2, 979.4950.
[0762] Synthesis of intermediate compound 64-b
[0763] Under an argon atmosphere, intermediate compound 64-a (9 g, 9.2 mmol), N-([1,1'-biphenyl]-4-yl-d9)-N-(3-(([1,1'-biphenyl]-4-yl-d9)oxy)-5-iodophenyl-4,6-d2)-[1,1':3',1”-tert-phenyl]-2'-amine (7.2 g, 9.2 mmol), Pd2dba3 (1.6 g, 1.9 mmol), tri-tert-butylphosphine (1.6 mL, 3.8 mmol), and sodium tert-butoxide (5.8 g, 60 mmol) were reacted. l) The solution was added to a 2 L flask and dissolved in 200 mL of o-xylene. The reaction solution was stirred at 140 °C for 2 hours. After cooling, water (1 L) and ethyl acetate (300 mL) were added for extraction, and the organic layer was collected, dried over anhydrous MgSO4, and filtered. The filtrate was subjected to reduced pressure to remove the solvent, and the obtained solid was purified and separated by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to obtain intermediate compound 64-b (white solid, 9.8 g, yield: 72%).
[0764] ESI-LCMS: [M] + :C 116 H 62D 31 N3OS2, 1640.
[0765] Synthesis of Compound 64
[0766] Under an argon atmosphere, intermediate compound 64-b (9.8 g, 6.6 mmol) was added to a 1 L flask and dissolved in 100 mL of o-dichlorobenzene. Then, BBr3 (4 equivalents) was added. The reaction solution was stirred at 140 °C for 12 hours. After cooling, triethylamine was added to terminate the reaction. The solvent was removed under reduced pressure, and the resulting solid was purified by column chromatography using silica gel with CH2Cl2 and hexane as developing solvent to yield compound 64 (yellow solid, 2.1 g, yield: 19%).
[0767] ESI-LCMS: [M] + :C 116 H 59 D 25 B3N3OS2, 1656.7976.
[0768] 1 H-NMR (CDCl3): d=8.15(m,6H),7.43(m,18H),7.39(m,3H),7.07(m,12H),6.93(s,2H),1.32(s,9H),1.22(s,9H).
[0769] By referring to the synthetic routes and raw materials, those skilled in the art can easily identify synthetic methods for fused-ring compounds other than those synthesized in Synthetic Examples 1 to 7.
[0770] Evaluation Example 1
[0771] For each compound in the examples and comparative examples, the HOMO energy level and the maximum absorption wavelength (λ) in solution were measured. Abs / 溶液 ) and maximum emission wavelength (λ) emi / 溶液 The results are shown in Table 1. The difference between the maximum wavelength at the energy absorption peak and the maximum wavelength at the energy emission peak (Stokes shift), the photoluminescence quantum yield (PLQY), and the full width at one-quarter peak (FWQM).
[0772] λ was measured using Labsolution UV-Vis software and a SHIMADZU UV-1800UV / Vis scanning spectrophotometer equipped with a deuterium / tungsten-halogen light source and silicon photodiodes. Abs λ was measured using FluorEssence software and a HORIBA fluoromax+ spectrometer equipped with a xenon light source and monochromator. emiAnd FWQM. HOMO energy levels were measured using Smart Manager software and a ZIVE LAB SP2 electrochemical workstation. PLQY measurements were performed using PLQY measurement software with a xenon source, monochromator, photon multichannel analyzer, and integrating sphere mounted on a Hamamatsu Quantaurus-QY Absolute PL quantum yield spectrometer.
[0773] Table 1
[0774]
[0775] Example 1
[0776] A 15Ω / cm anode will be formed on it. 2 The glass substrate (Corning's product) for the ITO electrode was cut to a size of 50mm × 50mm × 0.7mm, sonicated for 5 minutes each with isopropanol and (then) pure water, and then cleaned by irradiating it with ultraviolet light and exposing it to ozone for 30 minutes. The resulting ITO glass substrate was then mounted on a vacuum deposition apparatus.
[0777] NPD is deposited on the anode to form a structure with... A hole injection layer of a certain thickness is formed, and compound HT6 is deposited on the hole injection layer to form a hole injection layer with [missing information]. A hole transport layer of a certain thickness is formed, and CzSi is deposited on the hole transport layer to form a hole transport layer with a certain thickness. An electron blocking layer of a certain thickness.
[0778] Then, the host compound obtained by mixing compound HTH53 and compound ETH66 in a 1:1 weight ratio, PD33, and compound 2 were co-deposited in a weight ratio of 85:14:1 to form a compound with... A thick emission layer is formed, and TSPO1 is deposited on the emission layer to form a layer with [missing information]. A hole-blocking layer of a certain thickness was then deposited. Subsequently, TPBi was deposited on the hole-blocking layer to form a hole-blocking layer with [missing information]. An electron transport layer of a certain thickness is formed, and then LiF is deposited on the electron transport layer to form an electron transport layer with a certain thickness. An electron-injected layer of a certain thickness. Al is used to form an electron-injected layer with... A cathode of a certain thickness is formed, thus creating a LiF / Al electrode. Then, compound HT28 is deposited on the electrode to form a cathode with... A capping layer of varying thickness is applied to complete the fabrication of the light-emitting device. Each layer is formed using a vacuum deposition method.
[0779] Examples 2 to 7 and Comparative Examples 1 to 10
[0780] The light-emitting devices of Examples 2 to 7 and Comparative Examples 1 to 10 were manufactured in substantially the same manner as in Example 1, except that compounds 12, 17, 28, 35, 62, and 64, as well as comparative examples C-1 to C-10, were used instead of compound 2 in Example 1.
[0781]
[0782]
[0783] Evaluation Example 2
[0784] To evaluate the characteristics of each of the light-emitting devices manufactured according to Examples 1 to 7 and Comparative Examples 1 to 10, measurements were taken at 10 mA / cm². 2 The driving voltage, top emission efficiency (luminous efficacy), maximum emission wavelength, CIEy, and device lifetime at the specified current density were measured, and the results are shown in Table 2. The driving voltage and luminous efficacy of each of the light-emitting devices were measured using a V7000 OLED IVL testing system (Polaronix). To measure the device lifetime, the time taken to reach 95% of its initial brightness was measured for each of Examples 1 to 7 and Comparative Examples 1 to 10. The relative lifetime (Tb) was calculated as the ratio of the time taken to reach 95% of the initial brightness in Examples 1 to 7 and Comparative Examples 2 and 10 to the time taken to reach 95% of the initial brightness in Comparative Example 1. 95 ).
[0785] Table 2
[0786]
[0787]
[0788] As confirmed by Table 2, compared with the light-emitting devices of Comparative Examples 1 to 10, the light-emitting devices of Examples 1 to 7 each have a lower driving voltage, higher top emission efficiency and longer lifespan, which indicates that the light-emitting devices of Examples 1 to 7 exhibit better device characteristics than the light-emitting devices of Comparative Examples 1 to 10.
[0789] According to one or more embodiments, the use of the fused-ring compound represented by Formula 1 ensures the manufacture of light-emitting devices with high efficiency and long lifespan, as well as high-quality electronic devices and electronic equipment that accordingly include the light-emitting device. For example, compared with Comparative Examples 1 to 10, the light-emitting devices of Examples 1 to 7 exhibited lower driving voltages, higher top emission efficiency, and longer lifespans. These results (see Table 2 for details) demonstrate that the devices of Examples 1 to 7 exhibit superior performance characteristics, indicating that the use of specific compounds can enhance the efficiency and lifespan of light-emitting devices, resulting in high-quality electronic devices or electronic equipment.
[0790] In this disclosure, the terms “comprise(s) / comprising,” “include(s) / including,” or “have / has / having” will be understood to indicate the presence of a described feature, integer, step, operation, element, and / or component, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and / or groups thereof. Furthermore, the terms “comprise(s) / comprising,” “include(s) / including,” “have / has / having,” or other similar terms include or support the terms “consisting of,” and “substantially consisting of,” indicating the presence of a described feature, integer, step, operation, element, and / or component, while other features, integers, steps, operations, elements, components, and / or groups thereof are absent or substantially absent.
[0791] In the context of this application, and unless otherwise specified, the terms “use,” “using,” and “used” are to be regarded as synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.
[0792] Throughout this disclosure, when reference is made to placing a component (such as a layer, film, zone, or plate) "on" another component (such as a layer, film, zone, or plate), it will be understood that it may be directly on the other component (such as a layer, film, zone, or plate) or that the other component (such as a layer, film, zone, or plate) may be inserted therebetween. In some embodiments, "directly on" may mean that there is no other layer, film, zone, plate, etc. between the layer, film, zone, plate, etc. and the other component. For example, "directly on" may mean that two layers or two components are provided without the use of other components (such as adhesive components) between them.
[0793] In this disclosure, although the terms “first,” “second,” etc., may be used herein to describe one or more elements, components, areas, and / or layers, such elements, components, areas, and / or layers should not be limited by these terms. These terms are used only to distinguish one component from another.
[0794] As used herein, the singular forms “a,” “an,” “one,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise. Furthermore, in describing embodiments of this disclosure, the word “may” refers to “one or more embodiments of this disclosure.”
[0795] As used herein, the terms “substantially,” “about,” or similar terms are used as terms of approximation and not as terms of degree, and are intended to explain the inherent biases of measured or calculated values that would be recognized by one of ordinary skill in the art. “About” or “approximation” as used herein includes stated values and means within an acceptable range of deviations from a particular value, as determined by one of ordinary skill in the art considering the measurements under discussion and the errors associated with the measurement of a particular quantity (i.e., limitations of the measurement system). For example, “about” may mean within one or more standard deviations of the stated value, or within ±30%, ±20%, ±10%, or ±5% of the stated value.
[0796] Any numerical range set forth herein is intended to include all subranges with the same numerical precision that are covered within the set forth range. For example, the range “1.0 to 10.0” is intended to include all subranges between (and inclusive of) the set forth minimum value of 1.0 and the set forth maximum value of 10.0, i.e., all subranges with a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as 2.4 to 7.6. Any maximum numerical limit set forth herein is intended to include all lower numerical limits covered therein, and any minimum numerical limit set forth in this disclosure is intended to include all higher numerical limits covered therein. Accordingly, the applicant reserves the right to amend this disclosure (including the claims) to expressly set forth any subranges that are covered within the range expressly set forth herein.
[0797] The light-emitting devices, light-emitting apparatuses, display devices, electronic devices, electronic devices / apparatus, their manufacturing equipment, or any other related devices or components described herein according to embodiments of this disclosure can be implemented using any suitable hardware, firmware (e.g., application-specific integrated circuits), software, or a combination of software, firmware, and hardware. For example, various components of the device can be formed on an integrated circuit (IC) chip or on a separate IC chip. Furthermore, various components of the device can be implemented on a flexible printed circuit film, a tape package, or a printed circuit board (PCB), or formed on a substrate. Furthermore, various components of the device can be processes or threads running on one or more processors in one or more computing devices, executing computer program instructions, and interacting with other system components to perform the various functions described herein. The computer program instructions are stored in memory, which can be implemented using standard memory devices (e.g., random access memory (RAM) in the computing device). The computer program instructions can also be stored in other non-transitory computer-readable media (e.g., CD-ROMs or flash drives). Furthermore, those skilled in the art will recognize that, without departing from the scope of the embodiments of this disclosure, the functions of various computing devices may be combined or integrated into a single computing device, or the functions of a dedicated computing device may be distributed across one or more other computing devices.
[0798] It should be understood that the embodiments described herein are to be considered in a descriptive sense only and are not intended for limiting purposes. The description of features or aspects in each embodiment should generally be considered in light of other similar features or aspects that may be used in one or more embodiments. Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that one or more suitable changes in form and detail may be made therein without departing from the spirit and scope defined by the appended claims and their equivalents.
Claims
1. A light-emitting device, comprising: First electrode; A second electrode opposite to the first electrode; An interlayer comprising an emission layer between the first electrode and the second electrode; as well as Fused ring compounds represented by Formula 1: Formula 1 In Formula 1, Ar1 is a group represented by Formula 2. Formula 2 Furthermore, in Equations 1 and 2, CY1 to CY7 are each independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group, W1 represents a single bond, O, S, Se, Te, N(R) 1a ), C(R 1a (R) 1b ) or Si(R 1a (R) 1b ), W2 represents a single bond, O, S, Se, Te, N(R) 2a ), C(R 2a (R) 2b ) or Si(R 2a (R) 2b ), W3 represents single bonds, O, S, Se, Te, and N(R). 3a ), C(R 3a (R) 3b ) or Si(R 3a (R) 3b ), W4 represents single bonds, O, S, Se, Te, and N(R). 4a ), C(R 4a (R) 4b ) or Si(R 4a (R) 4b ), W5 represents single bonds, O, S, Se, Te, N(R). 5a ), C(R 5a (R) 5b ) or Si(R 5a (R) 5b ), W6 represents a single bond, O, S, Se, Te, N(R) 6a ), C(R 6a (R) 6b ) or Si(R 6a (R) 6b ), a1 to a6 are each independently 0 or 1. When a1 is 0, then *-(W1) a1 -*'Does not exist.' When a2 is 0, then *-(W2) a2 -*'Does not exist.' When a3 is 0, then *-(W3) a3 -*'Does not exist.' When a4 is 0, then *-(W4) a4 -*'Does not exist.' When a5 is 0, then *-(W5) a5 -*'Does not exist.' When a6 is 0, then *-(W6) a6 -*'Does not exist.' The sum of a1 to a3 is 1 or greater. The sum of a4 to a6 is 1 or greater. Y1 can be O, S, N(R8), N(Ar1), C(R8)(R9) or Si(R8)(R9). X 11 For C or N, X 12 For C(Z) 12 ) or N, X 13 For C(Z) 13 ) or N, X 14 For C(Z) 14 ) or N, X 15 For C(Z) 15 ) or N, and X 16 For C(Z) 16 ) or N, X 21 For C or N, X 22 For C(Z) 22 ) or N, X 23 For C(Z) 23 ) or N, X 24 For C(Z) 24 ) or N, X 25 For C(Z) 25 ) or N, and X 26 For C(Z) 26 ) or N, X 31 To X 33 Each can be independently represented as C or N. X 34 For C(Z) 34 ) or N, X 35 For C(Z) 35 ) or N, and X 36 For C(Z) 36 ) or N, X 41 and X 42 Each can be independently represented as C or N. X 43 For C(Z) 43 ) or N, X 44 For C(Z) 44 ) or N, X 45 For C(Z) 45 ) or N, and X 46 For C(Z) 46 () or N, where c1 is an integer selected from 0 to 10, n1 to n7 are each an independent integer selected from 0 to 10. When n1 is 2 or greater, the number of R1s of size n1 are independently identical or different from each other. When n² is 2 or greater, the number of R² units of n² are independently identical or different from each other. When n3 is 2 or greater, the number of R3s of n3 are independently identical or different from each other. When n⁴ is 2 or greater, the number of R⁴ of n⁴ are independently identical or different from each other. When n5 is 2 or greater, the number of R5s of size n5 are independently identical or different from each other. When n6 is 2 or greater, the number of R6 units of n6 are independently identical or different from each other. When n7 is 2 or greater, the number of R7s of size n7 are independently the same or different from each other. Optionally, some of the n1 R1s bond to each other to form a ring. Optionally, some of the n² R² units bond together to form a ring. Optionally, some of the n3 R3s bond together to form a ring. Optionally, some of the n4 R4s bond together to form a ring. Optionally, some of the n5 R5s bond together to form a ring. Optionally, some of the n6 R6 groups bond together to form a ring. Optionally, some of the n7 R7s bond together to form a ring. R1 to R9, R 1a To R 6a R 1b To R 6b Z 12 To Z 16 Z 22 To Z 26 Z 34 To Z 36 and Z 43 To Z 46 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, or hydrazone; Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof; Each of the following C3-Cs that are not substituted or are substituted by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aryl alkyl group; or C2-C 60 Heteroaryl groups, and In Equation 2, * represents the bonding site with the adjacent nitrogen atom.
2. The light-emitting device according to claim 1, wherein the first electrode is an anode. The second electrode is a cathode. The interlayer further includes a hole transport region between the first electrode and the emitter layer, and an electron transport region between the emitter layer and the second electrode. The hole transport region includes a hole injection layer, a hole transport layer, an emission assist layer, an electron blocking layer, or any combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, an electron control layer, or any combination thereof.
3. The light-emitting device according to claim 1, wherein the fused ring compound represented by formula 1 is in the interlayer.
4. The light-emitting device according to claim 1, wherein the fused ring compound represented by formula 1 is in the emitting layer.
5. The light-emitting device according to claim 1, wherein the light-emitting device further comprises a body and a dopant, and The dopant includes the fused ring compound represented by Formula 1.
6. An electronic device comprising a light-emitting device according to any one of claims 1 to 5.
7. The electronic device of claim 6, further comprising a color filter, a color conversion layer, a touch screen layer, a polarizing layer, or any combination thereof.
8. An electronic device comprising a light-emitting device according to any one of claims 1 to 5.
9. The electronic device according to claim 8, wherein the device is at least one of the following: flat panel display, curved display, computer monitor, medical monitor, television, billboard, indoor light, outdoor light, signal light, head-up display, fully transparent display, partially transparent display, flexible display, rollable display, foldable display, retractable display, laser printer, telephone, portable telephone, tablet PC, tablet computer, personal digital assistant, wearable device, laptop computer, digital camera, camcorder, viewfinder, microdisplay, 3D display, virtual reality display, augmented reality display, vehicle, video wall having multiple displays spliced together, theater screen, stadium screen, phototherapy device, and sign.
10. A fused-ring compound represented by Formula 1: Formula 1 in, In Formula 1, Ar1 is a group represented by Formula 2. Formula 2 Furthermore, in Equations 1 and 2, CY1 to CY7 are each independently C3-C 60 Carbocyclic or C1-C 60 Heterocyclic groups, W1 being single bonds, O, S, Se, Te, N(R) 1a ), C(R 1a (R) 1b ) or Si(R 1a (R) 1b W2 is a single bond, O, S, Se, Te, N (R) 2a ), C(R 2a (R) 2b ) or Si(R 2a (R) 2b W3 represents single bonds, O, S, Se, Te, and N (R). 3a ), C(R 3a (R) 3b ) or Si(R 3a (R) 3b W4 is a single bond, O, S, Se, Te, N (R) 4a ), C(R 4a (R) 4b ) or Si(R 4a (R) 4b W5 represents single bonds, O, S, Se, Te, and N (R). 5a ), C(R 5a (R) 5b ) or Si(R 5a (R) 5b ), W6 represents a single bond, O, S, Se, Te, N(R) 6a ), C(R 6a (R) 6b ) or Si(R 6a (R) 6b ), a1 to a6 are each independently 0 or 1. When a1 is 0, then *-(W1) a1 -*'Does not exist.' When a2 is 0, then *-(W2) a2 -*'Does not exist.' When a3 is 0, then *-(W3) a3 -*'Does not exist.' When a4 is 0, then *-(W4) a4 -*'Does not exist.' When a5 is 0, then *-(W5) a5 -*'Does not exist.' When a6 is 0, then *-(W6) a6 -*'Does not exist.' The sum of a1 to a3 is 1 or greater. The sum of a4 to a6 is 1 or greater. Y1 can be O, S, N(R8), N(Ar1), C(R8)(R9) or Si(R8)(R9). X 11 For C or N, X 12 For C(Z) 12 ) or N, X 13 For C(Z) 13 ) or N, X 14 For C(Z) 14 ) or N, X 15 For C(Z) 15 ) or N, and X 16 For C(Z) 16 ) or N, X 21 For C or N, X 22 For C(Z) 22 ) or N, X 23 For C(Z) 23 ) or N, X 24 For C(Z) 24 ) or N, X 25 For C(Z) 25 ) or N, and X 26 For C(Z) 26 ) or N, X 31 To X 33 Each can be independently represented as C or N. X 34 For C(Z) 34 ) or N, X 35 For C(Z) 35 ) or N, and X 36 For C(Z) 36 ) or N, X 41 and X 42 Each can be independently represented as C or N. X 43 For C(Z) 43 ) or N, X 44 For C(Z) 44 ) or N, X 45 For C(Z) 45 ) or N, and X 46 For C(Z) 46 () or N, where c1 is an integer selected from 0 to 10, n1 to n7 are each an independent integer selected from 0 to 10. When n1 is 2 or greater, the number of R1s of size n1 are independently identical or different from each other. When n² is 2 or greater, the number of R² units of n² are independently identical or different from each other. When n3 is 2 or greater, the number of R3s of n3 are independently identical or different from each other. When n⁴ is 2 or greater, the number of R⁴ of n⁴ are independently identical or different from each other. When n5 is 2 or greater, the number of R5s of size n5 are independently identical or different from each other. When n6 is 2 or greater, the number of R6 units of n6 are independently identical or different from each other. When n7 is 2 or greater, the number of R7s of size n7 are independently the same or different from each other. Optionally, some of the n1 R1s bond to each other to form a ring. Optionally, some of the n² R² units bond together to form a ring. Optionally, some of the n3 R3s bond together to form a ring. Optionally, some of the n4 R4s bond together to form a ring. Optionally, some of the n5 R5s bond together to form a ring. Optionally, some of the n6 R6 groups bond together to form a ring. Optionally, some of the n7 R7s bond together to form a ring. R1 to R9, R 1a To R 6a R 1b To R 6b Z 12 To Z 16 Z 22 To Z 26 Z 34 To Z 36 and Z 43 To Z 46 Each of the following groups is independently hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, unsubstituted, or substituted with at least one R. 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C2-C 60 alkenyl, unsubstituted or with at least one R 10a Replacement C2-C 60 Alkyne group, unsubstituted or with at least one R 10a Replacement C1-C 60 Alkyl, unsubstituted, or with at least one R 10a Replacement C3-C 60 Carbocyclic, unsubstituted, or with at least one R 10a Replacement C1-C 60 Heterocyclic groups, -C(Q1)(Q2)(Q3), -Si(Q1)(Q2)(Q3), -N(Q1)(Q2), -B(Q1)(Q2), -C(=O)(Q1), -S(=O)2(Q1) or -P(=O)(Q1)(Q2), R 10a for: Deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, amido, hydrazine, or hydrazone; Each of the following C1-C that is not substituted or is substituted: 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -Si(Q) 11 (Q) 12 (Q) 13 -N(Q) 11 (Q) 12 -B(Q) 11 (Q) 12 -C(=O)(Q) 11 -S(=O)2(Q) 11 -P(=O)(Q) 11 (Q) 12 ) or any combination thereof; Each of the following C3-Cs that are not substituted or are substituted by: 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl or C2-C 60 Heteroalkyl groups: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, C1-C 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic group, C1-C 60 Heterocyclic group, C6-C 60 Aryloxy group, C6-C 60 Arylthio, C7-C 60 Aryl alkyl, C2-C 60 heteroaryl, -Si(Q) 21 (Q) 22 (Q) 23 -N(Q) 21 (Q) 22 -B(Q) 21 (Q) 22 -C(=O)(Q) 21 -S(=O)2(Q) 21 -P(=O)(Q) 21 (Q) 22 ) or any combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-N(Q 31 )(Q 32 )、-B(Q 31 )(Q 32 )、-P(Q 31 )(Q 32 )、-C(=O)(Q 31 )、-S(=O)2(Q 31 )或-P(=O)(Q 31 )(Q 32 ), Q1 to Q3, Q 11 To Q 13 Q 21 To Q 23 and Q 31 To Q 33 Each of the following is independently: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl; cyano; nitro; each unsubstituted or replaced by deuterium, -F, cyano, C1-C 60 Alkyl, C1-C 60 C1-C substituted with alkoxy, phenyl, biphenyl or any combination thereof 60 Alkyl, C2-C 60 alkenyl, C2-C 60 Alkyne group, C1-C 60 Alkoxy, C3-C 60 Carbocyclic or C1-C 60 Heterocyclic group; C7-C 60 Aryl alkyl group; or C2-C 60 Heteroaryl groups, and In Equation 2, * represents the bonding site with the adjacent nitrogen atom.
11. The fused-ring compound according to claim 10, wherein the highest occupied molecular orbital energy level of the fused-ring compound represented by Formula 1 is -5.30 eV or less.
12. The fused-ring compound according to claim 10, wherein the fused-ring compound represented by Formula 1 has an asymmetric structure.
13. The fused-ring compound according to claim 10, wherein i) is selected from one of a1 to a3 and is 0, and the remainder are each 1, and ii) One of a4 to a6 is 0, and the rest are each 1.
14. The fused-ring compound according to claim 10, wherein the fused-ring compound represented by Formula 1 is a compound selected from any one of Formulas 1-1 to 1-6: Formula 1-1 Formula 1-2 Formula 1-3 Formula 1-4 Formula 1-5 Formula 1-6 In equations 1-1 to 1-6, Ar1, W1 to W6 and Y1 are each the same as those defined in Equation 1. R 11 To R 14 Each of them independently has the same constraint on R1 as in Equation 1. R 21 To R 24 Each of them independently has the same constraint as that for R2 in Equation 1. R 31 and R 32 Each of them independently has the same constraint on R3 as in Equation 1. R 41 To R 44 Each of them independently has the same constraint as that for R4 in Equation 1. R 51 To R 54 Each of them independently has the same constraint on R5 as in Equation 1. R 61 and R 62 Each is independently identical to the constraint on R6 in Equation 1, and R 71 To R 73 Each of them independently has the same limitation on R7 as in Equation 1.
15. The fused-ring compound according to claim 10, wherein Ar1 is a group represented by any one selected from formulas 2-1 to 2-8: And in equations 2-1 to 2-8, Z1 to Z3, Z'1 and Z'3 are each independently related to Z in Equation 1. 12 The constraints are the same, b1 and b2 are each integers selected from 0 to 5. b3 is an integer selected from 0 to 3. b1' is an integer selected from 0 to 4. b3' is an integer selected from 0 to 2, and * Indicates the bonding site with an adjacent nitrogen atom.
16. The fused-ring compound according to claim 10, wherein W1 is N(R) 1a ), W2 is 0. W5 is O, S, Se, Te, or N(R) 5a ),and W6 is a single bond, O, S, or N(R). 6a ).
17. The fused-ring compound according to claim 10, wherein Y1 is N(Ar1).
18. The fused-ring compound according to claim 10, wherein R1 to R9 are each independently: Hydrogen, deuterium, -F, or cyano; Each of the following is an unsubstituted or substituted methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, or 1,2-dimethylpropyl. Each of the following unsubstituted or substituted fluorenyl, phenyl, biphenyl, terphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, carbazole, azadibenzofuranyl, azadibenzothiophenyl, azacarbazole, phenoxazinyl, phenthiazinyl, or pyridoindolyl: deuterium, -F, -Cl, -Br, -I, hydroxyl, cyano, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, 2-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,2-dimethylpropyl, or combinations thereof; or -Si(Q1)(Q2)(Q3) or -N(Q1)(Q2).
19. The fused-ring compound according to claim 10, wherein R 1a To R 6a R 1b To R 6b R8 and R9 are each independently represented by any one of formulas 3-1 to 3-13: And in equations 3-1 to 3-13, T1 is N(R'1), C(R'1)(R'2), Si(R'1)(R'2), Se, Te, O, or S, and R'1 to R'5, R'7, R”4, and R”5 are each independently associated with the values in Equation 1 for R. 10a The constraints are the same, and d3 is an integer selected from 0 to 3. d4 is an integer selected from 0 to 4. d5 is an integer selected from 0 to 5. d7 is an integer selected from 0 to 7, and * Indicates the bonding site with adjacent atoms.
20. The fused-ring compound of claim 10, wherein the fused-ring compound represented by Formula 1 is selected from any one of compounds 1 to 80:
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KR1020240113739A